Name: 103-05-9|2-Methyl-4-phenyl-2-butanol|99%
Brand: Ambeed
SKU: A879719
Rating: 95 (30 reviews)

1
[ 103-05-9 ]
[ 108-24-7 ]
[ 103-07-1 ]

Yield	Reaction Conditions	Operation in experiment
67%	With dmap; triethylamine In dichloromethane at 20℃; for 24h;
	With sodium acetate at 135 - 139℃;
	With phosphoric acid

	With sodium acetate for 3h; Heating;
84 %Spectr.	With 1,1,7,7-tetramethyl-9-azajulolidine; triethylamine In dichloromethane at 20℃; for 11h; Inert atmosphere;	General Procedure for Substrate Scope Using TMAJ General procedure: To a solution of tertiary alcohol S4 (43.4 μmol) in CH2Cl2 (217.1 μL) were added 1.0 Msolution of TMAJ in CH2Cl2 (4.34 μL, 4.34 μmol), NEt3 (18.2 μL, 130 μmol) and Ac2O (8.21μL, 86.8 μmol) at room temperature. The reaction was monitored by TLC. When the reactionfinished, it was quenched with saturated aqueous solution of NH4Cl, and the mixture wasextracted with AcOEt (x3). The combined organic layers were dried over anhydrous MgSO4,filtered, and concentrated under reduced pressure. The residue was measured by 1H NMRwithout further purification, and the yield was determined by the integration ratio comparedwith pyrazine (3.48 mg, 43.4 μmol) as an internal standard.

Reference： [1]Nishimoto, Yoshihiro; Okita, Aya; Yasuda, Makoto; Baba, Akio [Organic Letters, 2012, vol. 14, # 7, p. 1846 - 1849]
[2]Kinsersskaja [Zhurnal Prikladnoi Khimii, 1940, vol. 13, p. 222,224][Chem.Abstr., 1940, p. 7859]
[3]Arai; Murata [Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1958, vol. 61, p. 563,565][Chem.Abstr., 1961, p. 10371]
[4]Gonzalez, Neil; Martin, Ignacio; Chuchani, Gabriel [Journal of Physical Chemistry, 1985, vol. 89, # 7, p. 1314 - 1318]
[5]Tsutsumi, Tomohiro; Saitoh, Arisa; Kasai, Tomoyo; Chu, MengYue; Karanjit, Sangita; Nakayama, Atsushi; Namba, Kosuke [Tetrahedron Letters, 2020, vol. 61, # 26]

2
[ 2550-26-7 ]
[ 75-16-1 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	In tetrahydrofuran; diethyl ether at 0℃; for 2h; Inert atmosphere;
74%	In diethyl ether at 0 - 20℃; Inert atmosphere;
	With vanadium(II)bis-N,N,N’,N’-tetramethylethylenediamine-dichloride; oxygen 1) THF, 20 deg C, 1 h; 2) THF, reflux, 15 h; Yield given. Multistep reaction;

	With vanadium(II)bis-N,N,N’,N’-tetramethylethylenediamine-dichloride; oxygen 1.) THF, 20 deg C, 2.) THF, 20 deg C, 3.) reflux, 15 h; Yield given. Multistep reaction;
	In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;
	In tetrahydrofuran for 0.666667h; Cooling with ice;
	In tetrahydrofuran for 0.666667h; Cooling with ice;

Reference： [1]Mikhael, Myriam; Guo, Wentao; Tantillo, Dean J.; Wengryniuk, Sarah E. [Advanced Synthesis and Catalysis, 2021, vol. 363, # 21, p. 4867 - 4875]
[2]Guo, Qihang; Ren, Xiang; Lu, Zhan [Organic Letters, 2019, vol. 21, # 4, p. 880 - 884]
[3]Owen,J.R.; Saunders,W.H. [Journal of the American Chemical Society, 1966, vol. 88, p. 5809 - 5816]
[4]Kataoka, Yasutaka; Akiyama, Hiroaki; Makihira, Isamu; Tani, Kazuhide [Journal of Organic Chemistry, 1996, vol. 61, # 18, p. 6094 - 6095]
[5]Kataoka, Yasutaka; Akiyama, Hiroaki; Makihira, Isamu; Tani, Kazuhide [Journal of Organic Chemistry, 1997, vol. 62, # 23, p. 8109 - 8113]
[6]Xu, Wentao; Ma, Junyang; Yuan, Xiang-Ai; Dai, Jie; Xie, Jin; Zhu, Chengjian [Angewandte Chemie - International Edition, 2018, vol. 57, # 32, p. 10357 - 10361][Angew. Chem., 2018, vol. 130, p. 10514 - 10518,5]
[7]Xing, Gang; Pan, Li; Yi, Ce; Li, Xiaoran; Ge, Xinyue; Zhao, Ying; Liu, Yichuang; Li, Jinyan; Woo, Anthony; Lin, Bin; Zhang, Yuyang; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 12, p. 2306 - 2314]
[8]Yi, Ce; Xing, Gang; Wang, Siqi; Li, Xiaoran; Liu, Yichuang; Li, Jinyan; Lin, Bin; Woo, Anthony Yiu-Ho; Zhang, Yuyang; Pan, Li; Cheng, Maosheng [Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 1]

3
[ 103-05-9 ]
[ 2049-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	(i) POCl₃, Py, (ii) H₂, Pd-C, EtOH; Multistep reaction;
	Multi-step reaction with 2 steps 1: PBr₃ 2: Mg / diethyl ether
	Multi-step reaction with 3 steps 1: SOCl₂ / CHCl₃ / 0.5 h 2: NaN₃ / dimethylformamide / 24 h / 90 °C 3: (thermolysis)

Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate / 3.5 h / 0 - 20 °C 2: tris(pentafluorophenyl)borate; triethylsilane / chloroform-d1 / 48 h / 20 °C

Reference： [1]Owen,J.R.; Saunders,W.H. [Journal of the American Chemical Society, 1966, vol. 88, p. 5809 - 5816]
[2]Sneeden,R.P.A.; Zeiss,H.H. [Journal of Organometallic Chemistry, 1971, vol. 26, p. 101 - 113]
[3]Abramovitch,R.A.; Kyba,E.P. [Journal of the American Chemical Society, 1974, vol. 96, p. 480 - 488]
[4]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]

4
[ 103-05-9 ]
[ 4912-92-9 ]

Yield	Reaction Conditions	Operation in experiment
41%	With fluorosulphonic acid In dichloromethane at -78℃; for 0.5h;
	With sulfuric acid
	(cyclization);

	With sulfuric acid
	With sulfuric acid

Reference： [1]Bright; Coxon; Steel [Journal of Organic Chemistry, 1990, vol. 55, # 4, p. 1338 - 1344] Barrow, Colin J.; Bright, Steven T.; Coxon, James M.; Steel, Peter J. [Journal of Organic Chemistry, 1989, vol. 54, # 11, p. 2542 - 2549]
[2]Warrick,P.; Saunders,W.H. [Journal of the American Chemical Society, 1962, vol. 84, p. 4095 - 4100] Owen,J.R.; Saunders,W.H. [Journal of the American Chemical Society, 1966, vol. 88, p. 5809 - 5816]
[3]Stock,L.M.; Young,P.E. [Journal of the American Chemical Society, 1972, vol. 94, p. 4247 - 4255]
[4]Sakhabutdinov, A.G.; Usmanova, A.G.; Proidakov, A.G.; Bazhenov, B.A.; Schmidt, F.K. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1525 - 1529][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1691 - 1696]
[5]Sakhabutdinov, A. G.; Usmanova, A. G.; Frolov, P. A.; Kushnarev, D. F.; Schmidt, F. K. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 8, p. 1452 - 1455][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1610 - 1614]

5
[ 103-05-9 ]
[ 52017-21-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With trimethylsilyl bromide In neat (no solvent) at 20℃; for 5h; Green chemistry; chemoselective reaction;	General procedure for the halo functionalization of organic compounds using halosilanes on half mmol scale General procedure: A mixture of alcohol (0.5 mmol) in the case of solids, which had been powedered for 1-2 min and halosilanes (0.55 mmol) was transferred to a 4 mL screw-capped vial, and stirred at rt or heated at 70-75 °C for 0.5 h-24 h. The progress of the reaction mixture was monitored by TLC. Upon completion of the reaction, the crude reaction mixture was cooled down to the room temperature and volatile product (TMS)2O was removed by evaporation at 30-35oC under reduced pressure and the remaining was analysed by 1H NMR. Finally, if necessary, the pure final product was obtained after column chromatography on dried silica. Detailed experimental information such as isolated yields, and spectroscopic and other identification data are given in Characterization Data of Isolated Final Products chapter in the SI.
99%	With hydrogen bromide; lithium bromide at 0 - 20℃;
87%	With hydrogen bromide; lithium bromide In water at 0 - 23℃;	2-Bromo-2-methyl-4-phenylbutane (S12) Procedure described by Dudnik et al.3 A solution of the alcohol (5.55 g, 33.8mmol, 1.0 equiv) in 48 wt% aqueous HBr (12.4 ml) was cooled to 0 °C, followed by the addition of LiBr (5.87 g, 67.6mmol, 2.0 equiv) at 0 °C. The reaction mixture was allowed to warm to 23 °C and stirred at this temperature untilcompletion of reaction. The reaction mixture was diluted with ether, washed with water, saturated sodium bicarbonateand brine. The organic layer was dried over sodium sulfate, concentrated in vacuo. The residue was purified by columnchromatography (silica pre-treated with 1% Et3N, 2% ether in hexanes, 2% ether in hexanes) to afford the title compoundas a clear liquid (6.70 g, 29.5 mmol, 87%). Spectral

80%	With tetra-(n-butyl)ammonium iodide; ethylene dibromide; triphenylphosphine at 60℃; for 2h; Sealed tube; Inert atmosphere;
74%	With hydrogen bromide In water at 25℃; for 24h;
	With phosphorus tribromide
	With hydrogen bromide at 20℃; for 3h;
	With hydrogen bromide; lithium bromide In dichloromethane; water at 0 - 20℃;
	With hydrogen bromide; lithium bromide In dichloromethane; water at 0 - 20℃; Inert atmosphere;

Reference： [1]Ajvazi, Njomza; Stavber, Stojan [Tetrahedron Letters, 2016, vol. 57, # 22, p. 2430 - 2433]
[2]Zhao, Huaibo; McMillan, Alastair J.; Constantin, Timothée; Mykura, Rory C.; Juliá, Fabio; Leonori, Daniele [Journal of the American Chemical Society, 2021, vol. 143, # 36, p. 14806 - 14813]
[3]Shim, Eunjae; Zakarian, Armen [Synlett, 2020, vol. 31, # 7, p. 683 - 686]
[4]Chen, Jia; Lin, Jin-Hong; Xiao, Ji-Chang [Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064]
[5]Location in patent: experimental part Someya, Hidenori; Yorimitsu, Hideki; Oshima, Koichiro [Tetrahedron, 2010, vol. 66, # 32, p. 5993 - 5999]
[6]Sneeden,R.P.A.; Zeiss,H.H. [Journal of Organometallic Chemistry, 1971, vol. 26, p. 101 - 113] Nishiyama; Kakushou; Sonoda [Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 12, p. 2779 - 2782]
[7]Vasil'ev, Andrei; Engman, Lars [Journal of Organic Chemistry, 2000, vol. 65, # 7, p. 2151 - 2162]
[8]Yu, Weijie; Chen, Long; Tao, Jiasi; Wang, Tao; Fu, Junkai [Chemical Communications, 2019, vol. 55, # 42, p. 5918 - 5921]
[9]Bellotti, Peter; Glorius, Frank; Heidrich, Bastian; Huang, Huan-Ming; Pflüger, Philipp M.; Schwarz, J. Luca [Journal of the American Chemical Society, 2020, vol. 142, # 22, p. 10173 - 10183]

6
[ 103-05-9 ]
[ 4830-95-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With chloro-trimethyl-silane In neat (no solvent) at 70 - 75℃; for 24h; Green chemistry; chemoselective reaction;	General procedure for the halo functionalization of organic compounds using halosilanes on half mmol scale General procedure: A mixture of alcohol (0.5 mmol) in the case of solids, which had been powedered for 1-2 min and halosilanes (0.55 mmol) was transferred to a 4 mL screw-capped vial, and stirred at rt or heated at 70-75 °C for 0.5 h-24 h. The progress of the reaction mixture was monitored by TLC. Upon completion of the reaction, the crude reaction mixture was cooled down to the room temperature and volatile product (TMS)2O was removed by evaporation at 30-35oC under reduced pressure and the remaining was analysed by 1H NMR. Finally, if necessary, the pure final product was obtained after column chromatography on dried silica. Detailed experimental information such as isolated yields, and spectroscopic and other identification data are given in Characterization Data of Isolated Final Products chapter in the SI.
93%	With hydrogenchloride In water at 25℃; for 24h;
92%	With indium(III) chloride; dimethylmonochlorosilane; benzil In dichloromethane at 20℃; for 12h; Inert atmosphere;

87%	With bismuth(III) chloride; chloro-trimethyl-silane In dichloromethane at 20℃; for 4h;
82%	With tetra-(n-butyl)ammonium iodide; 1,2-dichloro-ethane; triphenylphosphine at 120℃; for 0.5h; Sealed tube; Inert atmosphere;
	With thionyl chloride In chloroform for 0.5h;
	With hydrogenchloride In hexane
	Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 2: (Dichloroiodo)benzene / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
66 %Spectr.	With thionyl chloride In dichloromethane Inert atmosphere;

Reference： [1]Ajvazi, Njomza; Stavber, Stojan [Tetrahedron Letters, 2016, vol. 57, # 22, p. 2430 - 2433]
[2]Location in patent: experimental part Someya, Hidenori; Yorimitsu, Hideki; Oshima, Koichiro [Tetrahedron, 2010, vol. 66, # 32, p. 5993 - 5999]
[3]Wu, Xiangyu; Hao, Wei; Ye, Ke-Yin; Jiang, Binyang; Pombar, Gisselle; Song, Zhidong; Lin, Song [Journal of the American Chemical Society, 2018, vol. 140, # 44, p. 14836 - 14843]
[4]Nishimoto, Yoshihiro; Yasuda, Makoto; Baba, Akio [Organic Letters, 2007, vol. 9, # 24, p. 4931 - 4934]
[5]Chen, Jia; Lin, Jin-Hong; Xiao, Ji-Chang [Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064]
[6]Abramovitch,R.A.; Kyba,E.P. [Journal of the American Chemical Society, 1974, vol. 96, p. 480 - 488]
[7]Sneeden,R.P.A.; Zeiss,H.H. [Journal of Organometallic Chemistry, 1971, vol. 26, p. 101 - 113]
[8]Canestrari, Daniele; Lancianesi, Stefano; Badiola, Eider; Strinna, Chiara; Ibrahim, Hasim; Adamo, Mauro F. A. [Organic Letters, 2017, vol. 19, # 4, p. 918 - 921]
[9]Su, Justin Y.; Grünenfelder, Denise C.; Takeuchi, Kohei; Reisman, Sarah E. [Organic Letters, 2018, vol. 20, # 16, p. 4912 - 4916]

7
[ 100-42-5 ]
[ 67-64-1 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: styrene; acetone With N,N,N,N-tetraethylammonium tetrafluoroborate; zinc In N,N-dimethyl-formamide at 20℃; for 15h; Electrochemical reaction; Stage #2: With water In N,N-dimethyl-formamide Electrochemical reaction; regioselective reaction;
	(electrolysis);
	With sodium In diethyl ether

Reference： [1]Wu, Hongting; Chen, Weihao; Deng, Weijie; Yang, Ling; Li, Xinling; Hu, Yunfei; Li, Yibiao; Chen, Lu; Huang, Yubing [Organic Letters, 2022, vol. 24, # 6, p. 1412 - 1417]
[2]Makarochkina,S.M.; Tomilov,A.P. [Journal of general chemistry of the USSR, 1974, vol. 44, p. 2523 - 2525][Zhurnal Obshchei Khimii, 1974, vol. 44, p. 2566 - 2569]
[3]Kochi,J.K. [Journal of Organic Chemistry, 1963, vol. 28, p. 1960 - 1968]

8
[ 10439-23-3 ]
[ 103-05-9 ]
[ 79399-25-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With pyridine In diethyl ether at 0℃; for 3h;

Reference： [1]Babin, D.; Fourneron, J. D.; Harwood, L. M.; Julia, M. [Tetrahedron, 1981, vol. 37, p. 325 - 332]

9
[ 89881-71-0 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium fluoride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl acetamide at 60℃; for 6h;
62%	With tert-butyl 4-hydroxy-5-methylphenyl sulfide; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl acetamide at 60℃;

Reference： [1]Fleming, Ian; Henning, Rolf; Plaut, Howard [Journal of the Chemical Society. Chemical communications, 1984, # 1, p. 29 - 31]
[2]Fleming, Ian; Henning, Rolf; Parker, David C.; Plaut, Howard E.; Sanderson, Philip E. J. [Journal of the Chemical Society. Perkin transactions I, 1995, # 4, p. 317 - 338]

10
2-methyl-2-phenethyloxirane [ No CAS ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With ammonium formate In ethanol at 23℃; for 5h;

Reference： [1]Dragovich, Peter S.; Prins, Thomas, J.; Zhou, Ru [Journal of Organic Chemistry, 1995, vol. 60, # 15, p. 4922 - 4924]

11
[ 103-05-9 ]
[ 106-45-6 ]
[ 1025927-62-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.
82%	With sulfuric acid In water for 4h;

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]
[2]Guo, Yushen; Jenks, William S. [Journal of Organic Chemistry, 1997, vol. 62, # 4, p. 857 - 864]

12
[ 103-05-9 ]
[ 74-88-4 ]
[ 97231-89-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydride In tetrahydrofuran at 40℃; for 1.5h;

Reference： [1]Dinnocenzo; Zuilhof; Lieberman; Simpson; McKechney [Journal of the American Chemical Society, 1997, vol. 119, # 5, p. 994 - 1004]

13
[ 103-05-9 ]
[ 4489-84-3 ]
[ 6683-51-8 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In toluene for 5h; Heating; Yield given. Yields of byproduct given;
	With toluene-4-sulfonic acid In toluene for 5h; Heating; Yields of byproduct given. Title compound not separated from byproducts;
	With N-fluorobis(benzenesulfon)imide; triphenylphosphine In dichloromethane for 4h; Heating; Title compound not separated from byproducts;

	Stage #1: 4-phenyl-2-methyl-2-butanol With bromocyane; triphenylphosphine In dichloromethane at 20℃; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Cooling with ice; Inert atmosphere;
	With triphenylboroxine; tetrakis(triphenylphosphine)nickel⁽⁰⁾; water; acetophenone; 1,2-bis-(dicyclohexylphosphino)ethane In diethylene glycol dimethyl ether at 110℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;
	With tetrachloromethane; triphenylphosphine Inert atmosphere; Overall yield = 76 %Spectr.;
	Multi-step reaction with 2 steps 1: hydrogen bromide; lithium bromide / 0 - 20 °C 2: [CoCl₂(dmgH)2(pyridine)]; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; N-ethyl-N,N-diisopropylamine; potassium carbonate / acetonitrile / 16 h / 20 °C / Inert atmosphere; Sealed tube; Irradiation

Reference： [1]Von Doering; Benkhoff, Johannes; Carleton, Peter Smart; Pagnotta, Marco [Journal of the American Chemical Society, 1997, vol. 119, # 45, p. 10947 - 10955]
[2]Von Doering; Benkhoff, Johannes; Carleton, Peter Smart; Pagnotta, Marco [Journal of the American Chemical Society, 1997, vol. 119, # 45, p. 10947 - 10955]
[3]Giovanelli, Emerson; Doris, Eric; Rousseau, Bernard [Tetrahedron Letters, 2006, vol. 47, # 48, p. 8457 - 8458]
[4]Location in patent: experimental part Tarrade-Matha, Aurelie; Pillon, Florence; Doris, Eric [Synthetic Communications, 2010, vol. 40, # 11, p. 1646 - 1649]
[5]Lei, Chuanhu; Yip, Yong Jie; Zhou, Jianrong Steve [Journal of the American Chemical Society, 2017, vol. 139, # 17, p. 6086 - 6089]
[6]Su, Justin Y.; Grünenfelder, Denise C.; Takeuchi, Kohei; Reisman, Sarah E. [Organic Letters, 2018, vol. 20, # 16, p. 4912 - 4916]
[7]Zhao, Huaibo; McMillan, Alastair J.; Constantin, Timothée; Mykura, Rory C.; Juliá, Fabio; Leonori, Daniele [Journal of the American Chemical Society, 2021, vol. 143, # 36, p. 14806 - 14813]

14
[ 103-05-9 ]
[ 143422-89-3 ]
[ 142025-00-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With scandium tris(trifluoromethanesulfonate) In various solvent(s) at 20℃; for 0.5h;

Reference： [1]Suzuki; Watahiki; Oriyama [Tetrahedron Letters, 2000, vol. 41, # 46, p. 8903 - 8906]

15
2-(1,1-dimethyl-3-phenyl-propoxy)-tetrahydro-pyran [ No CAS ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With methanol; scandium tris(trifluoromethanesulfonate) In acetonitrile at 20℃; for 2h;

Reference： [1]Oriyama; Watahiki; Kobayashi; Hirano; Suzuki [Synthetic Communications, 2001, vol. 31, # 15, p. 2305 - 2311]

16
[ 110-87-2 ]
[ 103-05-9 ]
2-(1,1-dimethyl-3-phenyl-propoxy)-tetrahydro-pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With scandium tris(trifluoromethanesulfonate) In ethyl acetate at 20℃; for 24h;

Reference： [1]Watahiki, Tsutomu; Kikumoto, Hisashi; Matsuzaki, Masaya; Suzuki, Takeshi; Oriyama, Takeshi [Bulletin of the Chemical Society of Japan, 2002, vol. 75, # 2, p. 367 - 368]

17
tert-butyl-carbamic acid 1,1-dimethyl-3-phenyl-propyl ester [ No CAS ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With trimethylaluminum In 1,2-dichloro-ethane; toluene at -30 - 65℃; for 18h;

Reference： [1]El Kaim, Laurent; Grimaud, Laurence; Lee, Anabelle; Perroux, Yannick; Tirla, Cornelia [Organic Letters, 2004, vol. 6, # 3, p. 381 - 383]

18
[ 103-05-9 ]
[ 1609-86-5 ]
tert-butyl-carbamic acid 1,1-dimethyl-3-phenyl-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride In dichloromethane; water at 20℃; for 2h;

Reference： [1]El Kaim, Laurent; Grimaud, Laurence; Lee, Anabelle; Perroux, Yannick; Tirla, Cornelia [Organic Letters, 2004, vol. 6, # 3, p. 381 - 383]

19
[ 103-05-9 ]
[ 19031-66-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1,2-Diiodoethane; Selectfluor; 1,2-bis-(diphenylphosphino)ethane; zinc dibromide In acetonitrile at 20℃; for 0.25h; Sealed tube; Inert atmosphere;
65%	With pyridine hydrogenfluoride In tetrahydrofuran at 0℃; for 3h;
	With diethylamino-sulfur trifluoride In dichloromethane at -78 - 20℃;	General Procedure A General procedure: To a solution of alcohol (9.75 mmol) in dry CH2Cl2 (30 mL) at -78 °C, was added (diethylamino)sulfur trifluoride (2.60 mL, 3.14 g, 19.5 mmol, 2.00 equiv). The mixture was slowly warmed to room temperature and stirred for 2 h. The reaction was diluted with CH2Cl2, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo (< 20 °C). The residue was purified by silica gel chromatography (Petroleum ether) to afford the desired product.

	With diethylamino-sulfur trifluoride In dichloromethane at -78 - 20℃; for 1h;
	Multi-step reaction with 2 steps 1: diethyl ether / 0 - 20 °C 2: Selectfluor; disodium hydrogenphosphate; Ir[F(Me)ppy]2(dtbbpy)PF₆ / water; acetone / 1 h / 30 °C / Inert atmosphere; Sealed tube; Irradiation
	Multi-step reaction with 3 steps 1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 2: cesiumhydroxide monohydrate / tetrahydrofuran; water / 0.17 h / 20 °C / Inert atmosphere 3: Selectfluor / water; acetonitrile / 2 h / Inert atmosphere; Sealed tube; Irradiation
	Multi-step reaction with 2 steps 1: triethylamine; dmap / tetrahydrofuran / 20 °C 2: triethylamine tris(hydrogen fluoride); tris[2-(4,6-difluorophenyl)pyridinato-C²,N]-iridium(III) / dichloromethane / 20 °C / Inert atmosphere; Irradiation
	Multi-step reaction with 2 steps 1: 1,2-bis-(diphenylphosphino)ethane; 1,2-Diiodoethane / [D₃]acetonitrile / 0.02 h / 20 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 0.25 h / 20 °C / Sealed tube; Inert atmosphere
	Multi-step reaction with 2 steps 1: 1,2-bis-(diphenylphosphino)ethane; 1,2-Diiodoethane / acetonitrile / 0.25 h / 20 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 0.25 h / 20 °C / Sealed tube; Inert atmosphere
	Multi-step reaction with 2 steps 1: 1,2-bis-(diphenylphosphino)ethane; 1,2-Diiodoethane; zinc dibromide / acetonitrile / 0.25 h / 20 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 0.25 h / 20 °C / Sealed tube; Inert atmosphere
	Multi-step reaction with 2 steps 1: 1,2-bis-(diphenylphosphino)ethane; 1,2-Diiodoethane; zinc dibromide / acetonitrile / 0.25 h / 20 °C / Sealed tube; Inert atmosphere 2: Selectfluor; tetra-(n-butyl)ammonium iodide / acetonitrile / 0.25 h / 20 °C / Sealed tube; Inert atmosphere

Reference： [1]Zhang, Wei; Gu, Yu-Cheng; Lin, Jin-Hong; Xiao, Ji-Chang [Organic Letters, 2020, vol. 22, # 16, p. 6642 - 6646]
[2]Hirano, Koji; Yorimitsu, Hideki; Oshima, Koichiro [Organic Letters, 2004, vol. 6, # 26, p. 4873 - 4875]
[3]Dryzhakov, Marian; Richmond, Edward; Li, Guang; Moran, Joseph [Journal of Fluorine Chemistry, 2017, vol. 193, p. 45 - 51]
[4]Jaiswal, Amit K.; Prasad, Pragati K.; Young, Rowan D. [Chemistry - A European Journal, 2019, vol. 25, # 25, p. 6290 - 6294]
[5]González-Esguevillas, María; Miró, Javier; Jeffrey, Jenna L.; MacMillan, David W.C. [Tetrahedron, 2019, vol. 75, # 32, p. 4222 - 4227]
[6]Aguilar Troyano, Francisco José; Ballaschk, Frederic; Jaschinski, Marcel; Özkaya, Yasemin; Gómez-Suárez, Adrián [Chemistry - A European Journal, 2019, vol. 25, # 62, p. 14054 - 14058]
[7]Webb, Eric W.; Park, John B.; Cole, Erin L.; Donnelly, David J.; Bonacorsi, Samuel J.; Ewing, William R.; Doyle, Abigail G. [Journal of the American Chemical Society, 2020, vol. 142, # 20, p. 9493 - 9500]
[8]Zhang, Wei; Gu, Yu-Cheng; Lin, Jin-Hong; Xiao, Ji-Chang [Organic Letters, 2020, vol. 22, # 16, p. 6642 - 6646]
[9]Zhang, Wei; Gu, Yu-Cheng; Lin, Jin-Hong; Xiao, Ji-Chang [Organic Letters, 2020, vol. 22, # 16, p. 6642 - 6646]
[10]Zhang, Wei; Gu, Yu-Cheng; Lin, Jin-Hong; Xiao, Ji-Chang [Organic Letters, 2020, vol. 22, # 16, p. 6642 - 6646]
[11]Zhang, Wei; Gu, Yu-Cheng; Lin, Jin-Hong; Xiao, Ji-Chang [Organic Letters, 2020, vol. 22, # 16, p. 6642 - 6646]

20
pyridine-2-carboxylic acid 1,1-dimethyl-3-phenyl-propyl ester [ No CAS ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With zinc diacetate In methanol; dichloromethane at 38℃; for 30h;

Reference： [1]Ju, Yuel Baek; Shin, Yong-Joo; Heung, Bae Jeon; Kwan, Soo Kim [Tetrahedron Letters, 2005, vol. 46, # 31, p. 5143 - 5147]

21
[ 524-38-9 ]
[ 103-05-9 ]
2-(1,1-dimethyl-3-phenyl-propoxy)-isoindole-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;
64%	With boron trifluoride diethyl etherate In dichloromethane for 2h; Reflux; Inert atmosphere;
	With boron trifluoride diethyl etherate In dichloromethane; water at 0 - 20℃; for 1h;

Reference： [1]Palandoken, Hasan; Bocian, Chris M.; McCombs, Michelle R.; Nantz, Michael H. [Tetrahedron Letters, 2005, vol. 46, # 39, p. 6667 - 6669]
[2]Antien, Kevin; Geraci, Andrea; Parmentier, Michael; Baudoin, Olivier [Angewandte Chemie - International Edition, 2021, vol. 60, # 42, p. 22948 - 22955][Angew. Chem., 2021, vol. 133, # 42, p. 23130 - 23137]
[3]Kang, Taek; Kim, Heejeong; Kim, Jeung Gon; Chang, Sukbok [Chemical Communications, 2014, vol. 50, # 81, p. 12073 - 12075]

22
[ 103-05-9 ]
[ 1079-66-9 ]
[ 820961-79-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h;
98%	With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h;
95%	With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h;

91%	With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h;
	With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h;

Reference： [1]Kuroda, Kiichi; Hayashi, Yujiro; Mukaiyama, Teruaki [Tetrahedron, 2007, vol. 63, # 27, p. 6358 - 6364]
[2]Ikegai, Kazuhiro; Pluempanupat, Wanchai; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 5, p. 780 - 790]
[3]Ikegai, Kazuhiro; Pluempanupat, Wanchai; Mukaiyama, Teruaki [Chemistry Letters, 2005, vol. 34, # 5, p. 638 - 639]
[4]Aoki, Hidenori; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 8, p. 1255 - 1264]
[5]Masutani, Kouta; Minowa, Tomofumi; Hagiwara, Yoshiaki; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 7, p. 1106 - 1117]

23
[ 103-05-9 ]
[ 107-30-2 ]
2-methyl-4-phenyl-2-butyl methoxymethyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 12h;
	With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
	With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	4.2.1. Preparation of 1a-d, 1k, 1o, and 1p^10b General procedure: A solution of an alcohol (1 equiv), MOMCl (1.5-1.8 equiv), iPr2NEt (3-3.6 equiv), and DMAP (0.1 equiv) in dry CH2Cl2 (0.2-0.5 M) was stirred at 0 °C to rt under N2. After disappearance of the alcohol on TLC, the mixture was evaporated in vacuo. The residue was purified by flash SiO2 column chromatography to give a MOM/ether. 1a,10b 1b,23 1c,24 1d,25 1o,26 and 1p27 are known compounds.

	With N-ethyl-N,N-diisopropylamine In toluene at 5 - 25℃;
1.2 g	With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 60℃; Inert atmosphere; Schlenk technique;

Reference： [1]Berliner, Martin A.; Belecki, Katherine [Journal of Organic Chemistry, 2005, vol. 70, # 23, p. 9618 - 9621]
[2]Fujioka, Hiromichi; Kubo, Ozora; Senami, Kento; Minamitsuji, Yutaka; Maegawa, Tomohiro [Chemical Communications, 2009, # 29, p. 4429 - 4431]
[3]Location in patent: experimental part Fujioka, Hiromichi; Minamitsuji, Yutaka; Kubo, Ozora; Senami, Kento; Maegawa, Tomohiro [Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960]
[4]Berliner, Martin; Belecki, Katherine; Paquette, William D.; Wipf, Peter [Organic Syntheses, 2007, vol. 84, p. 102 - 110]
[5]Xu, Wentao; Ma, Junyang; Yuan, Xiang-Ai; Dai, Jie; Xie, Jin; Zhu, Chengjian [Angewandte Chemie - International Edition, 2018, vol. 57, # 32, p. 10357 - 10361][Angew. Chem., 2018, vol. 130, p. 10514 - 10518,5]

24
[ 2021-28-5 ]
[ 74-88-4 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With strontium In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Miyoshi, Norikazu; Matsuo, Tsuyoshi; Wada, Makoto [European Journal of Organic Chemistry, 2005, # 20, p. 4253 - 4255]

25
tetraphenylbismuth(V) fluoride [ No CAS ]
[ 103-05-9 ]
1,1-dimethyl-3-phenylpropyl phenyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-Methyldicyclohexylamine In toluene at 20℃; for 3h;

Reference： [1]Mukaiyama, Teruaki; Sakurai, Naoto; Ikegai, Kazuhiro [Chemistry Letters, 2006, vol. 35, # 10, p. 1140 - 1141]

26
[ 103-05-9 ]
[ 999-97-3 ]
[ 958640-39-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With iodine at 20℃; for 0.17h; Neat (no solvent); Air atmosphere;	4.2. Representative procedure of I₂-catalysed reaction of phenols, alcohols and carbohydrates with HMDS under SFRC (small scale) General procedure: Iodine (5.1 mg, 0.02 mmol) was added to phenol 1l (0.148 g, 1 mmol) or alcohol 3h (0.242 g, 1 mmol), followed by addition of HMDS (0.089 g, 0.55 mmol); the mixture was stirred at room temperature until the complete consumption of the starting material (TLC check). The crude reaction mixture was dissolved in 4 mL of hexane/TBME and stirred with the finely powdered Na2S2O3 until the disappearance of iodine. From this point on, two different scenarios are possible: a) The solids were filtered off and the solvent evaporated under the reduced pressure, yielding the crude product. In numerous cases, such products were practically pure; column chromatography and/or distillation improved their quality only slightly. b) A solution of a product in hexane/TBME mixture could be directly subjected to the column chromatography, without filtration of the solids. Caution: Although we experienced no problems when performing these reactions, care should taken due to the potential formation of NI3.
82%	With iodine In dichloromethane for 0.166667h;

Reference： [1]Location in patent: experimental part Jereb, Marjan [Tetrahedron, 2012, vol. 68, # 20, p. 3861 - 3867]
[2]Saito, Takahiro; Nishimoto, Yoshihiro; Yasuda, Makoto; Baba, Akio [Journal of Organic Chemistry, 2007, vol. 72, # 22, p. 8588 - 8590]

27
[ 100-42-5 ]
[ 67-63-0 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
50.3%	at 350℃; for 30h; Autoclave;	1 Example 1 A 400 ml autoclave was initially charged with 2.08 g (20.0 mmol) of styrene and 51.2 g (853 mmol) of isopropanol. The autoclave was closed and the reaction mixture was stirred at 350° C. (autogenous pressure 230 bar). After a reaction time of 2 h in each case, another 2.08 g (20.0 mmol) of styrene were added. After a total of 14 additions, corresponding to a total amount of styrene of 31.2 g (300 mmol), the reaction mixture was allowed to cool, and the autoclave was decompressed. Before each addition, a sample was taken and analyzed by means of gas chromatography for the composition thereof. In this way, the selectivity of the formation of 2-methyl-4-phenyl-2-butanol was determined based on the styrene used. The selectivities are reported in the table which follows: [table-us-00001-en] Styrene [mmol] 40 80 120 160 200 240 280 300 Reaction time[h] 4 8 12 16 20 24 28 30 Selectivity [%] 90.0 81.8 77.3 70.9 67.9 63.9 59.6 57.3 (0122) The reaction mixture was worked up by distillation. After removing the low boilers (in particular isopropanol), a crude product of purity >75% was obtained, which also comprised 2-methyl-4-phenyl-2-pentanol (1.0 GC area %). Further fine distillation gave 25.7 g (0.151 mol) of 4-phenyl-2-methylbutan-2-ol, corresponding to a yield of 50.3%. (0123) A mixture of 2-methyl-4-phenyl-2-butanol (99.8%) and 2-methyl-4-phenyl-2-pentanol (0.11 GC area %) obtained in the fine distillation was notable, in terms of odor, especially for an additional pleasant, faintly flowery note compared to the pure substance 2-methyl-4-phenyl-2-butanol.
70 % Chromat.	at 349.84℃; for 2h;
	at 410℃; Autoclave;	1 Step a) A solution of styrene in isopropanol (30% by weight, 200 g/h) was pumped through the laboratory plant at a mean temperature of 410° C. in the reactor. The conversion of styrene was 85.1%, and 12.5 g/h of 2-methyl-4-phenyl-2-butanol were obtained in the steady state. The samples were analyzed by means of gas chromatography.

Reference： [1]Current Patent Assignee: BASF SE - US2015/225325, 2015, A1 Location in patent: Paragraph 0121-0123
[2]Kamitanaka, Takashi; Hikida, Tatsuyoshi; Hayashi, Satoshi; Kishida, Nobuhiro; Matsuda, Tomoko; Harada, Tadao [Tetrahedron Letters, 2007, vol. 48, # 48, p. 8460 - 8463]
[3]Current Patent Assignee: BASF SE - US2013/72726, 2013, A1 Location in patent: Paragraph 0105; 0107

28
[ 103-05-9 ]
[ 6630-33-7 ]
[ 1160873-76-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 4-phenyl-2-methyl-2-butanol With Wilkinson's catalyst In toluene at 30℃; for 0.333333h; Inert atmosphere; Stage #2: ortho-bromobenzaldehyde With caesium carbonate In toluene at 30℃; for 0.333333h; Inert atmosphere; Stage #3: With boron trifluoride diethyl etherate In toluene at 30 - 50℃; Inert atmosphere;

Reference： [1]Zhang, Shu-Yu; Tu, Yong-Qiang; Fan, Chun-An; Jiang, Yi-Jun; Shi, Lei; Cao, Ke [Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2189 - 2193]

29
[ 1296645-18-5 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: C₁₅H₂₄O₃ With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: With water In diethyl ether; dichloromethane at 20℃; for 1h; Inert atmosphere; chemoselective reaction;	4.5. Deprotection of MOM, MEM, BOM, or SEM ether by TMSOTf (TESOTf)/2,2'-bipyridyl combination General procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2,2'-bipyridyl (3.0 equiv) in CH2Cl2 (0.2 M) at 0 °C under N2. The reaction mixture was stirred at the same temperature. After checking the disappearance of the starting material on TLC (30 min), H2O (2 mL/mmol) and Et2O (2 mL/mmol) were added to the reaction mixture and vigorously stirred. After disappearance of the high polar component was ascertained by TLC, the reaction mixture was extracted with CH2Cl2. The organic layer was washed with 3.5% HCl aq twice (for removal of 2,2'-bipyridyl) and with satd NaHCO3 aq. The combined organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography to give an alcohol 2. Silica gel 60 N (neutral) was used for the purification of substrate having TBS or Tr ethers instead of Merck Silica gel 60. Compounds 2e[31a], 2f[4a], 2g31b, 2h31c, 2i31d, 2j31e, and 2k28 are known compounds.

Reference： [1]Location in patent: experimental part Fujioka, Hiromichi; Minamitsuji, Yutaka; Kubo, Ozora; Senami, Kento; Maegawa, Tomohiro [Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960]

30
[ 1296645-32-3 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: C₁₉H₂₄O₂ With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: With water In dichloromethane at 20℃; for 1h; Inert atmosphere; chemoselective reaction;	4.5. Deprotection of MOM, MEM, BOM, or SEM ether by TMSOTf (TESOTf)/2,2'-bipyridyl combination General procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2,2'-bipyridyl (3.0 equiv) in CH2Cl2 (0.2 M) at 0 °C under N2. The reaction mixture was stirred at the same temperature. After checking the disappearance of the starting material on TLC (30 min), H2O (2 mL/mmol) and Et2O (2 mL/mmol) were added to the reaction mixture and vigorously stirred. After disappearance of the high polar component was ascertained by TLC, the reaction mixture was extracted with CH2Cl2. The organic layer was washed with 3.5% HCl aq twice (for removal of 2,2'-bipyridyl) and with satd NaHCO3 aq. The combined organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography to give an alcohol 2. Silica gel 60 N (neutral) was used for the purification of substrate having TBS or Tr ethers instead of Merck Silica gel 60. Compounds 2e[31a], 2f[4a], 2g31b, 2h31c, 2i31d, 2j31e, and 2k28 are known compounds.

Reference： [1]Location in patent: experimental part Fujioka, Hiromichi; Minamitsuji, Yutaka; Kubo, Ozora; Senami, Kento; Maegawa, Tomohiro [Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960]

31
[ 1296645-33-4 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: C₁₇H₃₀O₂Si With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: With water In dichloromethane at 20℃; for 1h; Inert atmosphere; chemoselective reaction;	4.5. Deprotection of MOM, MEM, BOM, or SEM ether by TMSOTf (TESOTf)/2,2'-bipyridyl combination General procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2,2'-bipyridyl (3.0 equiv) in CH2Cl2 (0.2 M) at 0 °C under N2. The reaction mixture was stirred at the same temperature. After checking the disappearance of the starting material on TLC (30 min), H2O (2 mL/mmol) and Et2O (2 mL/mmol) were added to the reaction mixture and vigorously stirred. After disappearance of the high polar component was ascertained by TLC, the reaction mixture was extracted with CH2Cl2. The organic layer was washed with 3.5% HCl aq twice (for removal of 2,2'-bipyridyl) and with satd NaHCO3 aq. The combined organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography to give an alcohol 2. Silica gel 60 N (neutral) was used for the purification of substrate having TBS or Tr ethers instead of Merck Silica gel 60. Compounds 2e[31a], 2f[4a], 2g31b, 2h31c, 2i31d, 2j31e, and 2k28 are known compounds.

Reference： [1]Location in patent: experimental part Fujioka, Hiromichi; Minamitsuji, Yutaka; Kubo, Ozora; Senami, Kento; Maegawa, Tomohiro [Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960]

32
[ 3587-60-8 ]
[ 103-05-9 ]
[ 1296645-32-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	4.4.1. Preparation of BOM ethers 4a-c General procedure: A solution of alcohol 2 (1.0 equiv), BOMCl (2.0 equiv), iPr2NEt (3.0 equiv), and DMAP (0.1 equiv) in dry CH2Cl2 (0.3-0.5 M) was stirred at 0 °C to rt under N2. After disappearance of 2 on TLC, the mixture was added satd NH4Cl aq and the resulting solution was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography to give BOM ether 4.

Reference： [1]Location in patent: experimental part Fujioka, Hiromichi; Minamitsuji, Yutaka; Kubo, Ozora; Senami, Kento; Maegawa, Tomohiro [Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960]

33
[ 3970-21-6 ]
[ 103-05-9 ]
[ 1296645-18-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	4.3.1. Preparation of MEM ethers 3a-c, 3e General procedure: A solution of alcohol 2 (1.0 equiv), MEMCl (2.0 equiv), iPr2NEt (3.0 equiv), and DMAP (0.1 equiv) in dry CH2Cl2 (0.2-0.5 M) was stirred at 0 °C to rt under N2. After disappearance of 2 on TLC, satd NH4Cl aq was added to the mixture and the resulting solution was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography to give MEM ether 3. 3a is a known compound.10b

Reference： [1]Location in patent: experimental part Fujioka, Hiromichi; Minamitsuji, Yutaka; Kubo, Ozora; Senami, Kento; Maegawa, Tomohiro [Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960]

34
2-methyl-4-phenyl-2-butyl methoxymethyl ether [ No CAS ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 2-methyl-4-phenyl-2-butyl methoxymethyl ether With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: With water In diethyl ether; dichloromethane at 20℃; for 2h; Inert atmosphere; chemoselective reaction;	4.5. Deprotection of MOM, MEM, BOM, or SEM ether by TMSOTf (TESOTf)/2,2'-bipyridyl combination General procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2,2'-bipyridyl (3.0 equiv) in CH2Cl2 (0.2 M) at 0 °C under N2. The reaction mixture was stirred at the same temperature. After checking the disappearance of the starting material on TLC (30 min), H2O (2 mL/mmol) and Et2O (2 mL/mmol) were added to the reaction mixture and vigorously stirred. After disappearance of the high polar component was ascertained by TLC, the reaction mixture was extracted with CH2Cl2. The organic layer was washed with 3.5% HCl aq twice (for removal of 2,2'-bipyridyl) and with satd NaHCO3 aq. The combined organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography to give an alcohol 2. Silica gel 60 N (neutral) was used for the purification of substrate having TBS or Tr ethers instead of Merck Silica gel 60. Compounds 2e[31a], 2f[4a], 2g31b, 2h31c, 2i31d, 2j31e, and 2k28 are known compounds.

Reference： [1]Location in patent: experimental part Fujioka, Hiromichi; Minamitsuji, Yutaka; Kubo, Ozora; Senami, Kento; Maegawa, Tomohiro [Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960]

35
[ 103-05-9 ]
(3-iodo-3-methyl-n-butyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With methanesulfonic acid; sodium iodide In acetonitrile at 0 - 20℃; for 0.5h;
60%	With 1,2-Diiodoethane; triphenylphosphine In acetonitrile at 60℃; for 2h; Sealed tube; Inert atmosphere;
45%	With methanesulfonic acid; sodium iodide In acetonitrile at 0 - 20℃; Inert atmosphere;

	With methanesulfonic acid; sodium iodide In acetonitrile at 0 - 20℃; for 2h;
	With methanesulfonic acid; sodium iodide In acetonitrile at 0 - 20℃; for 0.5h; Inert atmosphere;
91 %Spectr.	With 1,2-Diiodoethane; 1,2-bis-(diphenylphosphino)ethane In acetonitrile at 20℃; for 0.25h; Sealed tube; Inert atmosphere;
	With methanesulfonic acid; sodium iodide In acetonitrile at 0 - 20℃; Schlenk technique;
	With methanesulfonic acid; sodium iodide In acetonitrile at 0 - 20℃; for 0.5h;

Reference： [1]Kurandina, Daria; Rivas, Mónica; Radzhabov, Maxim; Gevorgyan, Vladimir [Organic Letters, 2018, vol. 20, # 2, p. 357 - 360]
[2]Chen, Jia; Lin, Jin-Hong; Xiao, Ji-Chang [Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064]
[3]Dudnik, Alexander S.; Fu, Gregory C. [Journal of the American Chemical Society, 2012, vol. 134, # 25, p. 10693 - 10697]
[4]Chen, Yanchi; Su, Lei; Gong, Hegui [Organic Letters, 2019, vol. 21, # 12, p. 4689 - 4693]
[5]Chierchia, Matteo; Xu, Peilin; Lovinger, Gabriel J.; Morken, James P. [Angewandte Chemie - International Edition, 2019, vol. 58, # 40, p. 14245 - 14249][Angew. Chem., 2019, vol. 131, p. 14383 - 14387,5]
[6]Zhang, Wei; Gu, Yu-Cheng; Lin, Jin-Hong; Xiao, Ji-Chang [Organic Letters, 2020, vol. 22, # 16, p. 6642 - 6646]
[7]Liu, Xian-Guan; Dong, Ci-Shuang; Li, Fei; Zhang, Bo [Organic Letters, 2021, vol. 23, # 10, p. 4002 - 4007]
[8]Maiti, Saikat; Rhlee, Joon Ho; Maiti, Saikat [Chemical Communications, 2021, vol. 57, # 86, p. 11346 - 11349]

36
[ 103-05-9 ]
[ 83926-73-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen at 40℃; for 12h; Autoclave;	1 Step b) A 300 ml autoclave was initially charged with 100 g of a discharge from step a), which was concentrated to a 2-methyl-4-phenyl-2-butanol content of 50%, and 5 g of the catalyst according to EP1317959 example 1B. The autoclave was purged three times with nitrogen and then hydrogenation was effected at 40° C. and hydrogen pressure 150 bar for 12 hours. After 12 hours, the discharge was analyzed by means of gas chromatography (30 m column material DB1, internal diameter: 0.25 mm, film thickness: 0.25 μm, temperature program 50° C.-5 min isothermal; 6° C./min.□290° C.-219 min. isothermal). The conversion of methyl-4-phenyl-2-butanol was >99.9%; [0113] the selectivity for 4-cyclohexyl-2-methyl-2-butanol was 97.7%.
3900 g	With ruthenium on aluminium oxide; hydrogen at 60 - 90℃; for 8h; Autoclave; Inert atmosphere; Large scale;	5 Example 5 Hvdrogenation of CM to 4-cvclohexyl-2-methyl-2-butanol Example 5 Hvdrogenation of CM to 4-cvclohexyl-2-methyl-2-butanol 6 Liter high-pressure stirred reactor (Parr Engineering) was charged with 4100 grams of CM and 14 grams of 5% RU/AI2O3 catalyst. Reactor was closed, then vacuumed and pressurized with nitrogen to 3 bar. Then, the pressure was vented and the vacuum was broken with hydrogen and the reactor was pressurized to 5 bar. Under stirring, the reactor was pressurized with hydrogen to 14 bar. Temperature was raised to 60°C. Hydrogenation was run for 8 hours at 60-90°C and 14 bar. At this point, GC analysis showed the residual content of CM of 0.12%. The reaction mix was filtered from the catalyst and distilled on a fractionating column, resulting in 3900 g olfactively acceptable 4-cyclohexyl-2-methyl-2-butanol.

Reference： [1]Current Patent Assignee: BASF SE - US2013/72726, 2013, A1 Location in patent: Paragraph 0111-0113
[2]Current Patent Assignee: Firmenich International SA - WO2014/1266, 2014, A1 Location in patent: Page/Page column 9

37
[ 103-25-3 ]
[ 75-16-1 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
54%	In tetrahydrofuran at 0℃; for 1h;	4.10.2. 2-Methyl-4-phenylbutan-2-ol (12) To a stirred of THF solution (12mL) of methyl 3-phenylpropanoate 1.0g (6.1mmol), 12.2mL of methylmagnesium bromide (1M in THF) was added dropwise at 0°C. After addition, the reaction mixture was stirred for 1h and then diluted with brine and extracted with ethyl acetate. The organic layers were combined, dried with MgSO4, and concentrated by reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:5) to afford 2-methyl-4-phenylbutan-2-ol in a 54.0% yield.

Reference： [1]Ho, Jinn-Hsuan; Lee, Ya-Wen; Chen, Ying-Zhe; Chen, Pin-Sian; Liu, Wei-Qi; Ding, Yi-Shun [Tetrahedron, 2013, vol. 69, # 35, p. 7325 - 7332]

38
[ 104174-42-7 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
92 %Chromat.	With 5%-palladium/activated carbon; hydrogen at 90℃; for 5h; Autoclave; Inert atmosphere;	4 Example 4 Hydrolysis of DDD (4,4-dimethyl-2,6-diphenyl-l,3-dioxane) to 2-methyl-4-phenyl-2,4- butanediol (HCM) and HCM Example 4 Hydrolysis of DDD (4,4-dimethyl-2,6-diphenyl-l,3-dioxane) to 2-methyl-4-phenyl-2,4- butanediol (HCM) and HCM hydrogenolysis to 2-methyl-4-phenyl-2-butanol A 450 ml high pressure reactor (autoclave) was charged with 72 g DDD and 74.5 g of deionized water had been charged. Reactor was closed, sealed, vacuumed and purged with N2. Then, under stirring, temperature was gradually raised to 200°C and kept at 200°C for 2.5 hours. At that point, the pressure inside the autoclave was approximately 15 bar. Then reactor was cooled down, and its contents discharged. The organic phase was separated from the aqueous phase and flash distilled under vacuum. Distilled material was fractionated in vacuum on a packed distillation column to recover benzaldehyde and to deliver a crude HCM. 73.8 g of the crude HCM together with 0.36 g of 5% Pd/carbon catalyst (50% moist) were charged into the cleaned and dried autoclave. The reactor was purged 3 times with N2, then 3 times with hydrogen. Under stirring the hydrogen pressure was brought to 14 bar and the temperature to 90°C. After 5 hours, the reactor was cooled down and its contents analyzed. The reaction mix contained (area% GC) 92% CMt (CM), 0.3% HCM, and 4.8% toluene. The reaction mix was then filtered from the catalyst and fractionally distilled to produce olfactively acceptable CM.

Reference： [1]Current Patent Assignee: Firmenich International SA - WO2014/1266, 2014, A1 Location in patent: Page/Page column 8-9

39
[ 17383-99-2 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
1800 g	With phosphoric acid; 5%-palladium/activated carbon; hydrogen at 80 - 105℃; for 36h; Inert atmosphere; Autoclave; Large scale;	2 Example 2 Hydrogenolysis of DDD (4,4-dimethyl-2,6-diphenyl-l,3-dioxane) to CM (2-methyl-4- phenyl-2-butanol) Example 2 Hydrogenolysis of DDD (4,4-dimethyl-2,6-diphenyl-l,3-dioxane) to CM (2-methyl-4- phenyl-2-butanol) In a 6 liter high pressure reactor (autoclave) where charged 4100 g DDD, 20.5 g of 5% Pd/C catalyst (50% wet), and 16.4 g of 85% H3PO4. The reactor was closed, sealed, vacuumed and purged 3 times with N2 at 4 bar. Then, it was vacuumed and filled with pressurized hydrogen to 10 bar. This procedure was repeated twice. Then, under stirring, hydrogen pressure was increased to 15 bar, and temperature gradually raised to 80°C. Hydrogenation had been run for a total of 36 hours at 80-105°C, after which the reaction was cooled down to 80°C and filtered from the catalyst. The aqueous phase was withdrawn and the organic phase washed from the residual acid with a NaHC03 solution. Washed organic phase was charged into the fractionating still. After toluene was removed at slight vacuum (-250 mbar), the remainder of the material was distilled at progressively increasing vacuum (up to 2 mbar eventually) and vapor temperature 60-80°C, recovering a total of 1800 g of CM. It was suitable for the use as aroma chemical, or for further hydrogenation processes.
	Multi-step reaction with 2 steps 1: sodium carbonate; water / 4.5 h / 200 °C / 12001.2 Torr / Autoclave; Inert atmosphere 2: hydrogen; 5%-palladium/activated carbon / 5 h / 90 °C / 10501.1 Torr / Autoclave; Inert atmosphere

Reference： [1]Current Patent Assignee: Firmenich International SA - WO2014/1266, 2014, A1 Location in patent: Page/Page column 8
[2]Current Patent Assignee: Firmenich International SA - WO2014/1266, 2014, A1

40
[ 558-30-5 ]
[ 1589-82-8 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With copper(l) iodide In tetrahydrofuran; toluene at -10 - 0℃; for 3h;	2 Preparation of 2-methyl-4-phenylbutan-2-ol 13.92 g of copper(I) iodide were added to the supernatant obtained according to example 1, and the flask was cooled to -10° C. Then, 52.70 g of isobutylene oxide were added gradually over a period of 1 hour using a dropping funnel, and the temperature was maintained between -10° C. and -6° C. A mild exotherm was observed during this latter process. After stirring the mixture for a further 2 hours at 0° C., a sample was taken for analysis by gas chromatography. This sample was worked up with ammonium chloride solution. The reaction mixture was worked up by addition of 400 ml of saturated ammonium chloride solution, and 200 ml of toluene were added. The organic phase was separated off and washed twice with 400 ml each time of saturated ammonium chloride solution. After drying over magnesium sulfate, the product was obtained by distillation in vacuo with a purity of >97%. A total of 88.9 g of 2-methyl-4-phenylbutan-2-ol were obtained, corresponding to a yield of 74%.

Reference： [1]Current Patent Assignee: BASF SE - US2014/73819, 2014, A1 Location in patent: Paragraph 0027

41
[ 103-05-9 ]
2,4,6-tris(4-methoxybenzyloxy)-1,3,5-triazine [ No CAS ]
[ 1402544-07-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With (1S)-10-camphorsulfonic acid In tetrahydrofuran at 20℃; for 8h; Reflux;	p-Methoxybenzyl 2-Methyl-4-phenylbutan-2-yl Ether (2d) To a solution of 2-methyl-4-phenylbutan-2-ol (74.0 mg, 0.451 mmol) and TriBOT-PM (441.1 mg, 0.901 mmol) in THF (1.50 mL), CSA (15.7 mg, 0.0676 mmol) was added at r.t. The mixture was heated to reflux and additional TriBOT-PM was added after 1.5 h (132.3 mg, 0.270 mmol), 3 h (66.2 mg, 0.135 mmol), 4.5 h (66.2mg, 0.135 mmol), and 6 h (44.1 mg, 0.0901 mmol), respectively. The mixture was stirred for an additional 2 h, and then it was cooled to r.t. and diluted with Et2O (10 mL), washed with H2O (23 mL), 10% K2CO3 (3 × 10 mL), and brine (10 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure.The residue was purified by column chromatography (hexane-EtOAc, 40:1 to 19:1) to afford 2d (107.9 mg, 94%) as a clear colorless oil.

Reference： [1]Yamada, Kohei; Fujita, Hikaru; Kitamura, Masanori; Kunishima, Munetaka [Synthesis, 2013, vol. 45, # 21, p. 2989 - 2997]

42
C₂₃H₂₆O₂ [ No CAS ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In aq. phosphate buffer; dichloromethane at 0 - 20℃; for 2h;
91%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In aq. phosphate buffer; dichloromethane at 0 - 20℃; for 2h;	9 EXAMPLE 9 Deprotection of NAPOM Ether 3b EXAMPLE 9 Deprotection of NAPOM Ether 3b (0055) The NAPOM ether 3b (167 mg, 0.50 mmol) was dissolved in a dichloromethane-pH 7.0 phosphate buffer solution 18:1 mixed solvent (5 mL), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ, 170 mg, 0.75 mmol) was added at 0° C., and the mixture was vigorously stirred at room temperature for 2 hours. The mixture was diluted with ether at 0° C., and then a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium thiosulfate aqueous solution were added to stop the reaction. (0056) The obtained mixture was subjected to extraction with ether three times, and the organic phases were combined, washed with a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (pentane/ether=10/1→5/1) to obtain the alcohol 3a (74.5 mg, 0.454 mmol, 91%) as a pale yellow oily material. Alcohol 3a: 1H-NMR (400 MHz, CDCl3): δ 7.30-7.27 (m, 2H), 7.21-7.16 (m, 3H), 2.72-2.68 (m, 2H), 1.82-1.77 (m, 2H), 1.29 (s, 6H). (This chart agrees with the chart of a commercial product.)

Reference： [1]Sato, Takuya; Oishi, Tohru; Torikai, Kohei [Organic Letters, 2015, vol. 17, # 12, p. 3110 - 3113]
[2]Current Patent Assignee: KYUSHU UNIVERSITY - US2017/305809, 2017, A1 Location in patent: Paragraph 0055; 0556

43
[ 914300-10-0 ]
[ 103-05-9 ]
C₂₃H₂₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine; calcium chloride In dichloromethane at 20℃; for 32.5h; Inert atmosphere;
96%	Stage #1: 4-phenyl-2-methyl-2-butanol With N-ethyl-N,N-diisopropylamine; calcium chloride In dichloromethane at 20℃; for 0.5h; Stage #2: 2-((chloromethoxy)methyl)naphthalene In dichloromethane at 20℃; for 32.5h;	3 EXAMPLE 3 NAPOM Ether 3b EXAMPLE 3 NAPOM Ether 3b (0048) Finely ground calcium chloride (196 mg, 1.77 mmol) and ethyldiisopropylamine (1.29 mL, 7.14 mmol) were added to a dichloromethane (3 mL) solution of an alcohol 3a (196 mg, 1.19 mmol), and the mixture was stirred at room temperature for 30 minutes. NAPOM chloride (92%, 799 mg, 3.56 mmol) was added, and the mixture was further stirred at room temperature for 32.5 hours. The mixture was cooled to 0° C. and diluted with ether, and then water was added to stop the reaction. The obtained mixture was subjected to extraction with ether three times, and the organic phases were combined, washed with a saturated potassium hydrogen sulfate aqueous solution and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=50/1→30/1) to obtain a NAPOM ether 3b (383 mg, 1.15 mmol, 96%) as a colorless oily material. NAPOM ether 3b: (0049) 1H-NMR (400 MHz, CDCl3): δ 7.83-7.80 (m, 4H), 7.49-7.44 (m, 3H), 7.27-7.24 (m, 2H), 7.19-7.15 (m, 3H), 4.94 (s, 2H), 4.83 (s, 2H), 2.74-2.69 (m, 1H), 1.89-1.84 (m, 2H), 1.35 (s, 6H).

Reference： [1]Sato, Takuya; Oishi, Tohru; Torikai, Kohei [Organic Letters, 2015, vol. 17, # 12, p. 3110 - 3113]
[2]Current Patent Assignee: KYUSHU UNIVERSITY - US2017/305809, 2017, A1 Location in patent: Paragraph 0048; 0049

44
[ 103-05-9 ]
[ 106-54-7 ]
(4-chlorophenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.
253 mg	With boron trifluoride diethyl etherate at 0 - 20℃; for 3.5h;

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]
[2]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]

45
[ 79-37-8 ]
[ 103-05-9 ]
2-((2-methyl-4-phenylbutan-2-yl)oxy)-2-oxoacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: oxalyl dichloride; 4-phenyl-2-methyl-2-butanol In diethyl ether at 0 - 23℃; for 18h; Inert atmosphere; Stage #2: With water In diethyl ether at 0℃;
92%	In diethyl ether at 0 - 20℃;	3.1. General Procedure A. Direct synthesis of oxalic acids with oxalyl chloride. General procedure: A round-bottom flask was charged with the corresponding alcohol (1.0 equiv) followed by the addition of Et2O (0.1 M). The solution was cooled to 0 °C. Next, oxalyl chloride (2.0 equiv) was added dropwise. The homogeneous reaction mixture was allowed to warm to ambient temperatureand stir for 1-18 h. The reaction was cooled to 0 °C and quenched by slow addition of H2O (100.0 equiv). After stirring for 1 h at room temperature, the resulting mixture was transferred to a separatory funnel, and the aqueous layer mixture was extracted with three portions of Et2O. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure affording the desired oxalic acid. All the oxalates were used without further purification.
	In diethyl ether at 0 - 20℃; for 18.1667h; Inert atmosphere;

In diethyl ether at 0 - 20℃; for 18h; Inert atmosphere;

Reference： [1]Nawrat, Christopher C.; Jamison, Christopher R.; Slutskyy, Yuriy; MacMillan, David W. C.; Overman, Larry E. [Journal of the American Chemical Society, 2015, vol. 137, # 35, p. 11270 - 11273]
[2]González-Esguevillas, María; Miró, Javier; Jeffrey, Jenna L.; MacMillan, David W.C. [Tetrahedron, 2019, vol. 75, # 32, p. 4222 - 4227]
[3]Kiyokawa, Kensuke; Watanabe, Tomoki; Fra, Laura; Kojima, Takumi; Minakata, Satoshi [Journal of Organic Chemistry, 2017, vol. 82, # 22, p. 11711 - 11720]
[4]Amos, Stephanie G. E.; Cavalli, Diana; Le Vaillant, Franck; Waser, Jerome [Angewandte Chemie - International Edition, 2021, vol. 60, # 44, p. 23827 - 23834][Angew. Chem., 2021, vol. 133, # 44, p. 24020 - 24027]

46
[ 2550-26-7 ]
[ 676-58-4 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;
72%	In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;	Synthesis of 2-methyl-4-phenylbutan-2-ol (25) To a solution of S13 (1.00 mL, 6.68 mmol) in THF (33 mL) was added 3.0 M THF solution of MeMgCl (3.34 mL, 10.0 mmol) at 0 °C, and the mixture was stirred for 10 minutes. The reaction was quenched with saturated aqueous solution of NH4Cl, and the mixture was extracted with AcOEt (x3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (Hexane/AcOEt = 4/1) to give 25 (786 mg, 4.79 mmol, 72%) as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 7.34-7.20 (m, 5H), 2.71-2.67 (m, 2H), 1.80 (d, J = 17.4 Hz, 1H), 1.78-1.74 (m, 2H), 1.27 (s, 6H). This 1H NMR data is identical with that of ref 6.

Reference： [1]Murray, James I.; Spivey, Alan C. [Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 3825 - 3830]
[2]Tsutsumi, Tomohiro; Saitoh, Arisa; Kasai, Tomoyo; Chu, MengYue; Karanjit, Sangita; Nakayama, Atsushi; Namba, Kosuke [Tetrahedron Letters, 2020, vol. 61, # 26]

47
[ 109-87-5 ]
[ 103-05-9 ]
2-methyl-4-phenyl-2-butyl methoxymethyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: Dimethoxymethane With trifluorormethanesulfonic acid; acetyl chloride at 0 - 20℃; for 0.166667h; Stage #2: 4-phenyl-2-methyl-2-butanol With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h;	10 Example 10 Synthesis of 2-methyl-4-phenyl-2-butyl methoxymethyl ether (XVIII) Acetyl chloride 0.427 mL (0.006 mol) and dimethoxymethane 0.534 mL (0.006 mol) were added to an 8 mL reaction flask. 0.016 mL (1.8x10-4 mol) of trifluoromethanesulfonic acid was slowly added at 0°C. The reaction was then allowed to proceed to room temperature at 20°C for 10 minutes. The reaction solution was added directly to 2-methyl-4-phenyl-2-butanol (XVII) 0.493 g (0.003 mol) and N,N-diisopropylethylamine 2.0 mL (0.012 mol) in 3 mL of dichloromethane for 0.5 h. The reaction was monitored to completion using thin layer chromatography (TLC). The reaction system was poured into 10 mL of saturated sodium bicarbonate solution. 5 mL of methylene chloride was added. After sufficiently stirring for 10 minutes, liquid separation. Each time the aqueous phase was extracted twice with 5 mL of dichloromethane. The organic phases were combined then washed with a saturated saline solution. Dried over anhydrous sodium sulfate. The filtrate was dried to give 0.615 g of a colorless transparent liquid 2-methyl-4-phenyl-2-butyl methoxymethyl ether (XVIII), yield 98%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN104710286, 2016, B Location in patent: Paragraph 0061; 0062; 0063; 0064

48
[ 13667-12-4 ]
[ 13041-70-8 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
92%Spectr.; 8%Spectr.	With [{Ir(H)((rac)-BINAP)}2(μ-Cl)3]Cl; hydrogen; In 1,4-dioxane; at 80℃; under 750.075 Torr; for 16h;	General procedure: Iridium dinuclear complex (2.4 mol, 1.0 mol%) and alkyne (0.24 mmol) were added to a glasstube in the reactor and the tube was charged with argon gas. Dry 1,4-dioxane (1.5 mL) was addedinto a glass tube in the reactor, and replaced argon gas with H2 gas. The reaction mixture wasstirred for periodic time under optimal conditions. After removal of solvent, the mixture andphenanthrene were dissolved into CDCl3. Yield was determined by 1H NMR analysis usingphenanthrene as an internal standard and reference to literatures.

Reference： [1]Chemistry Letters,2016,vol. 45,p. 866 - 868

49
[ 1942-30-9 ]
[ 1694-20-8 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 93 %Spectr. 2: 6 %Spectr.	With [{Ir(H)((rac)-BINAP)}2(μ-Cl)3]Cl; hydrogen In 1,4-dioxane at 90℃; for 16h;	General procedure for the Ir-catalyzed semi-hydrogenation of alkynes General procedure: Iridium dinuclear complex (2.4 mol, 1.0 mol%) and alkyne (0.24 mmol) were added to a glasstube in the reactor and the tube was charged with argon gas. Dry 1,4-dioxane (1.5 mL) was addedinto a glass tube in the reactor, and replaced argon gas with H2 gas. The reaction mixture wasstirred for periodic time under optimal conditions. After removal of solvent, the mixture andphenanthrene were dissolved into CDCl3. Yield was determined by 1H NMR analysis usingphenanthrene as an internal standard and reference to literatures.

Reference： [1]Higashida, Kosuke; Mashima, Kazushi [Chemistry Letters, 2016, vol. 45, # 8, p. 866 - 868]

50
[ 2170-06-1 ]
[ 19372-00-0 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 79 %Spectr. 2: 7 %Spectr.	With [{Ir(H)((rac)-BINAP)}2(μ-Cl)3]Cl; hydrogen In 1,4-dioxane at 80℃; for 16h;	General procedure for the Ir-catalyzed semi-hydrogenation of alkynes General procedure: Iridium dinuclear complex (2.4 mol, 1.0 mol%) and alkyne (0.24 mmol) were added to a glasstube in the reactor and the tube was charged with argon gas. Dry 1,4-dioxane (1.5 mL) was addedinto a glass tube in the reactor, and replaced argon gas with H2 gas. The reaction mixture wasstirred for periodic time under optimal conditions. After removal of solvent, the mixture andphenanthrene were dissolved into CDCl3. Yield was determined by 1H NMR analysis usingphenanthrene as an internal standard and reference to literatures.

Reference： [1]Higashida, Kosuke; Mashima, Kazushi [Chemistry Letters, 2016, vol. 45, # 8, p. 866 - 868]

51
[ 1129-65-3 ]
[ 6111-82-6 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 90 %Spectr. 2: 10 %Spectr.	With [{Ir(H)((rac)-BINAP)}2(μ-Cl)3]Cl; hydrogen In 1,4-dioxane at 80℃; for 16h;	General procedure for the Ir-catalyzed semi-hydrogenation of alkynes General procedure: Iridium dinuclear complex (2.4 mol, 1.0 mol%) and alkyne (0.24 mmol) were added to a glasstube in the reactor and the tube was charged with argon gas. Dry 1,4-dioxane (1.5 mL) was addedinto a glass tube in the reactor, and replaced argon gas with H2 gas. The reaction mixture wasstirred for periodic time under optimal conditions. After removal of solvent, the mixture andphenanthrene were dissolved into CDCl3. Yield was determined by 1H NMR analysis usingphenanthrene as an internal standard and reference to literatures.

Reference： [1]Higashida, Kosuke; Mashima, Kazushi [Chemistry Letters, 2016, vol. 45, # 8, p. 866 - 868]

52
[ 1719-19-3 ]
[ 103-05-9 ]
[ 57132-28-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 87 %Spectr. 2: 6 %Spectr.	With [{Ir(H)((rac)-BINAP)}2(μ-Cl)3]Cl; hydrogen In 1,4-dioxane at 80℃; for 16h;	General procedure for the Ir-catalyzed semi-hydrogenation of alkynes General procedure: Iridium dinuclear complex (2.4 mol, 1.0 mol%) and alkyne (0.24 mmol) were added to a glasstube in the reactor and the tube was charged with argon gas. Dry 1,4-dioxane (1.5 mL) was addedinto a glass tube in the reactor, and replaced argon gas with H2 gas. The reaction mixture wasstirred for periodic time under optimal conditions. After removal of solvent, the mixture andphenanthrene were dissolved into CDCl3. Yield was determined by 1H NMR analysis usingphenanthrene as an internal standard and reference to literatures.

Reference： [1]Higashida, Kosuke; Mashima, Kazushi [Chemistry Letters, 2016, vol. 45, # 8, p. 866 - 868]

53
[ 558-30-5 ]
[ 100-39-0 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: benzyl bromide With iodine; magnesium In tetrahydrofuran at 46 - 56℃; Inert atmosphere; Stage #2: 2-methyl-1,2-epoxypropane With copper(l) iodide In tetrahydrofuran at -10 - 0℃; for 2h;	1; 2 Preparation of 2-methyl-4-phenylbutan-2-ol An A 6 l reactor (HWS Labortechnik Mainz) equipped with an external heating mantleWas brought to an inactive condition with argon.A suspension of 88.71 g of magnesium in 1500 ml of tetrahydrofuran was placed in a flask and 0.50 g of iodine was added with stirring. This gave a brownish-yellowish suspension. Subsequently, 250.00 g of benzyl bromide was gradually added to the suspension using a dropping funnel over 165 minutes.As a result, the solution became colorless. After initially heating the content of the flask to 56 ° C., the reaction progressed exothermically. The addition rate of benzyl bromide was adjusted so that the temperature of the flask contents was maintained between 46 ° C. and 56 ° C.After addition of the benzyl bromide and cooling of the contents of the flask to room temperature was complete, the supernatant was decanted into a second inerted flask. Was added to the supernatant obtained according to Example 1 and the flask was cooled to -10 ° C.52.70 g of isobutylene oxide was then slowly added over 1 hour using a dropping funnel and the temperature was maintained between -10 ° C. and -6 ° C.A mild exotherm was observed during the subsequent process.After stirring the mixture for a further 2 hours at 0 ° C., the sample was taken for analysis by gas chromatography.This sample was treated with ammonium chloride solution.The reaction mixture was worked up by adding 400 ml of saturated ammonium chloride solution and 200 ml of toluene was added.The organic phase was separated and washed twice with 400 ml each of saturated ammonium chloride solution.After drying over magnesium sulfate, the product was obtained by distillation under reduced pressure and the purity was over 97% (> 97%). A total amount of 88.9 g of 2-methyl-4-phenylbutan-2-ol corresponding to a yield of 74% was obtained.

Reference： [1]Current Patent Assignee: BASF SE - JP2015/527383, 2015, A Location in patent: Paragraph 0028; 0029

54
[ 103-05-9 ]
[ 115262-01-6 ]
(3-(difluoromethoxy)-3-methylbutyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium hydrogen difluoride In dichloromethane; water at 20℃; for 10h;
81%	With potassium hydrogenfluoride In water at 20℃; for 12h;	Typical Procedures (Method 6.3) General procedure: Into a 10-mL plastic tube containing 2-methyl-4-phenylbutan-2-ol (1t) (82 mg, 0.5 mmol) and KHF 2 (312 mg, 4.0 mmol) was added water (0.3 mL). After stirring for a while to dissolve KHF 2 , TMSCF 2 Br (2) (312 μL, 2.0 mmol) was added. The reaction mixture was vigorously stirred at room temperature for 12 h, and then diluted with CH2Cl2 (2.0 mL) for determination of the 19F NMR yield. For characterization of the product, the above reaction mixture was further treated with water (3.0 mL) and extracted with CH2Cl2 (3 × 2.0 mL). The organic layers were combined and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel (heptane/CH2Cl2, 5:1, v/v) to afford the desired product 3t in 81% yield (87 mg).

Reference： [1]Xie, Qiqiang; Ni, Chuanfa; Zhang, Rongyi; Li, Lingchun; Rong, Jian; Hu, Jinbo [Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3206 - 3210][Angew. Chem., 2017, vol. 129, # 12, p. 3254 - 3258]
[2]Zhang, Rongyi; Ni, Chuanfa; Xie, Qiqiang; Hu, Jinbo [Tetrahedron, 2020, vol. 76, # 50]

55
[ 103-05-9 ]
[ 108-98-5 ]
[ 79399-21-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 1h; Schlenk technique; Inert atmosphere;

Reference： [1]Canestrari, Daniele; Lancianesi, Stefano; Badiola, Eider; Strinna, Chiara; Ibrahim, Hasim; Adamo, Mauro F. A. [Organic Letters, 2017, vol. 19, # 4, p. 918 - 921]

56
[ 103-05-9 ]
6-(benzyloxy)-1,3-dimethyl-1,3,5-triazine-2,4(1H,3H)-dione [ No CAS ]
benzyl 1,1-dimethyl-3-phenylpropyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With 2,6-di-tert-butylpyridinium trifluoromethanesulfonate In 1,4-dioxane at 50℃; for 3h; Molecular sieve; Inert atmosphere;
83%	With toluene-4-sulfonic acid In 1,4-dioxane at 50℃; for 3h; Molecular sieve; Inert atmosphere;	5 Benzylation of 2-(2-chloroethoxy)ethanol General procedure: Molecular sieve 5A (6.7 mg) activated in a test tube, 2- (2-chloroethoxy) ethanol (42.2 μL, 0.400 mmol), compound (I-1) (118.7 mg, 0.480 mmol) Trifluoromethanesulfonic acid (3.51 μL, 0.0400 mmol) and 1,4-dioxane (1.33 mL) were added and the mixture was stirred at room temperature under a nitrogen atmosphere for 4 hours. After completion of the reaction, the reaction solution was added to a saturated aqueous solution of sodium bicarbonate, extracted twice with ethyl acetate (10 mL), and washed with saturated brine (20 mL). After washing the obtained organic layer with sodium sulfate, ethyl acetate was distilled off, and the residue was separated and purified by silica gel column chromatography to obtain benzyl 2- (2-chloroethoxy) ethyl ether (76.9 mg, yield 90 %) Was obtained.

Reference： [1]Fujita, Hikaru; Kakuyama, Satoshi; Kunishima, Munetaka [European Journal of Organic Chemistry, 2017, vol. 2017, # 4, p. 833 - 839]
[2]Current Patent Assignee: KANAZAWA UNIVERSITY - JP2017/81832, 2017, A Location in patent: Paragraph 0127; 0129-0131

57
[ 103-05-9 ]
[ 88045-68-5 ]
C₂₃H₂₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 19h;	1-Naphthylmethoxymethyl ether 3c. To a solution of 2-methyl-4-phenyl-2-butanol 3a (246.4 mg, 1.50 mmol) in anhydrous CH2Cl2 (3 mL) were added i-Pr2NEt (1.55 mL, 9.00 mmol) and 1-naphthylmethoxymethyl chloride (89%, 1.04 g, 4.50 mmol) at rt. After being stirred at rt for 19 h, the reaction mixture was diluted with ether and quenched with H2O at 0 °C. The residual mixture was extracted with ether and the organic layer was washed with saturated aqueous solutions of KHSO4 and NaCl, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (hexane/ethyl acetate = 50/1 → 30/1) to give NAPOMI ether 3d (480.3 mg, 1.44 mmol, 96%) as a colorless oil.
96%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 19h;	21 EXAMPLE 21 1-NAPOM Ether 3c EXAMPLE 21 1-NAPOM Ether 3c (0069) Ethyldiisopropylamine (1.55 mL, 9.00 mmol) and 1-NAPOM chloride (89%, 1.04 g, 4.50 mmol) were added to a dichloromethane (3 mL) solution of the alcohol 3a (246 mg, 1.50 mmol) at room temperature, and the mixture was further stirred at room temperature for 19 hours. The mixture was cooled to 0° C. and diluted with ether, and then water was added to stop the reaction. The obtained mixture was subjected to extraction with ether three times, and the organic phases were combined, washed with a saturated potassium hydrogen sulfate aqueous solution and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=50/1→30/1) to obtain a 1-NAPOM ether 3c (480 mg, 1.44 mmol, 96%) as a colorless oily material. 1-NAPOM ether 3c: 1H-NMR (400 MHz, CDCl3): d 8.11 (d, J=8.2 Hz, 1H), 7.87 (d, J=7.8 Hz, 1H), 7.81 (d, J=8.2 Hz, 1H), 7.54-7.41 (m, 4H), 7.25-7.23 (m, 2H), 7.20-7.15 (m, 3H), 5.12 (s, 2H), 4.95 (s, 2H), 2.74-2.70 (m, 2H), 1.89-1.84 (m, 2H), 1.34 (s, 6H).

Reference： [1]Sato, Takuya; Joh, Yohei; Oishi, Tohru; Torikai, Kohei [Tetrahedron Letters, 2017, vol. 58, # 23, p. 2178 - 2181]
[2]Current Patent Assignee: KYUSHU UNIVERSITY - US2017/305809, 2017, A1 Location in patent: Paragraph 0069

58
[ 103-05-9 ]
[ 3163-27-7 ]
C₂₂H₂₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: 4-phenyl-2-methyl-2-butanol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-(bromomethyl)naphthalene In N,N-dimethyl-formamide at 20 - 70℃; for 26h; Inert atmosphere;	1-Naphthylmethyl ether 3b. Under argon atmosphere, to a solution of 2-methyl-4-phenyl-2-butan- ol 3a (1.15 g, 7.00 mmol) in anhydrous DMF (7.0 mL) were added NaH (420 mg, 10.5 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 30 min, and then 1-naphthylmethyl bromide (1.70 g, 7.70 mmol) was added. After stirring at rt for 23 h, the reaction was heated to 70 °C with oilbath. After being stirred at 70 °C for 3 h, the reaction mixture was diluted with ether and quenched with saturated aqueous solution of NH4Cl at 0 °C. The residual mixture was extracted with ether and the organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (hexane/ethyl acetate = 40/1 → 10/1 → 3/1) to give NAPI ether 3b (1.24 g, 4.07 mmol, 58%) as a colorless oil with recovery of 2-methyl-4-phenyl-2-butanol 3a (378 mg, 2.30 mmol, 33%) as a pale yellow oil.

Reference： [1]Sato, Takuya; Joh, Yohei; Oishi, Tohru; Torikai, Kohei [Tetrahedron Letters, 2017, vol. 58, # 23, p. 2178 - 2181]

59
C₂₂H₂₄O [ No CAS ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 0 - 20℃; for 1.5h;	Deprotection of 1-Naphthylmethyl ether 3b. DDQ (68.1 mg, 0.300 mmol) was added to a solution of 3b (30.4 mg, 0.100 mmol) in a mixed solvent of CH2Cl2 (800 mL) and H2O (200 mL) at 0 °C. After the mixture was stirred vigorously at 0 °C to rt for 1.5 h, the reaction mixture was diluted with ether and quenched with saturated aqueous solutions of NaHCO3 and Na2S2O3 at 0 °C. The residual mixture was extracted with ether and the organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (pentane/ether = 2/1) to give 2-methyl-4-phenyl-2-butanol 3a (16.6 mg, 0.101 mmol, quantitative).

Reference： [1]Sato, Takuya; Joh, Yohei; Oishi, Tohru; Torikai, Kohei [Tetrahedron Letters, 2017, vol. 58, # 23, p. 2178 - 2181]

60
C₂₃H₂₆O₂ [ No CAS ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 0 - 20℃; for 27h; Reflux;	Deprotection of 1-Naphthylmethoxymethyl ether 3c (3a) (Table 3, Entry 7). DDQ (68.1 mg, 0.30 mmol) was added to a solution of 3c (33.4 mg, 0.10 mmol) in a mixed solvent of CH2Cl2 (800 mL) and H2O (200 mL) at 0 °C. The mixture was stirred vigorously at 0 °C for 30 min, then warm to rt. After being stirred at rt for 26.5 h, the reaction mixture was diluted with ether and quenched with saturated aqueous solutions of NaHCO3 and Na2S2O3 at 0 °C. The residual mixture was extracted with ether and the organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (pentane/ether = 10/1 → 5/1 → 3/1) to give 2-methyl-4-phenyl-2-buta-nol 3a (16.2 mg, 0.0986 mmol, 99%) as a pale yellow oil.
99%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 0 - 20℃; for 27h;	24 EXAMPLE 24 Deprotection of 1-NAPOM Ether 3c EXAMPLE 24 Deprotection of 1-NAPOM Ether 3c (0072) The 1-NAPOM ether 3c (33.4 mg, 0.100 mmol) was dissolved in a dichloromethane-H2O 4:1 mixed solvent (1 mL), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ, 68.1 mg, 0.300 mmol) was added at 0° C., and the mixture was vigorously stirred at room temperature for 27 hours. The mixture was diluted with ether at 0° C., and then a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium thiosulfate aqueous solution were added to stop the reaction. The obtained mixture was subjected to extraction with ether three times, and the organic phases were combined, washed with a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (pentane/ether=10/1→5/1→3/1) to obtain the alcohol 3a (16.2 mg, 0.0986 mmol, 99%) as a pale yellow oily material. Alcohol 3a: 1H-NMR (400 MHz, CDCl3): d 7.30-7.27 (m, 2H), 7.21-7.16 (m, 3H), 2.72-2.68 (m, 2H), 1.82-1.77 (m, 2H), 1.29 (s, 6H). (This chart agrees with the chart of a commercial product.)

Reference： [1]Sato, Takuya; Joh, Yohei; Oishi, Tohru; Torikai, Kohei [Tetrahedron Letters, 2017, vol. 58, # 23, p. 2178 - 2181]
[2]Current Patent Assignee: KYUSHU UNIVERSITY - US2017/305809, 2017, A1 Location in patent: Paragraph 0072

61
C₂₃H₂₆O₂ [ No CAS ]
[ 4780-79-4 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 100% 2: 37%	With ammonium cerium (IV) nitrate In water; acetone at 0 - 20℃; for 121h;	Deprotection of 1-Naphthylmethoxymethyl ether 3c (3a) (Table 3, Entry 8). CAN (110 mg, 0.200 mmol) was added to a solution of 3c (33.4 mg, 0.100 mmol) in a mixed solvent of acetone (900 mL) and H2O (100 mL) at 0 °C. After stirring at 0 °C to rt for 6.5 h, additional CAN (110 mg, 0.200 mmol) was added at 0 °C. After being stirred at 0 °C to rt for 20 h, the reaction mixture was diluted with ether and quenched with saturated aqueous solutions of NaHCO3 and Na2S2O3 at 0 °C. The residual mixture was extracted with ether and the organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (pentane/ether = 10/1 → 5/1 → 3/1) to give an inseparable mixture of 2-methyl-4-phenyl-2-butanol 3a and 1-naphthalenemethanol (22.2 mg) as a pale yellow oil. The yields of these compounds were calculated by 1H-NMR to be 2-methyl-4-phenyl-2-butanol 3a (quantitative) and 1-naphthalenemethanol (37%).

Reference： [1]Sato, Takuya; Joh, Yohei; Oishi, Tohru; Torikai, Kohei [Tetrahedron Letters, 2017, vol. 58, # 23, p. 2178 - 2181]

62
[ 103-05-9 ]
[ 7285-83-8 ]
benzyl 1,1-dimethyl-3-phenylpropyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With toluene-4-sulfonic acid In 1,4-dioxane at 50℃; for 3h; Molecular sieve; Inert atmosphere;	5 Benzylation of 2-(2-chloroethoxy)ethanol General procedure: Molecular sieve 5A (6.7 mg) activated in a test tube, 2- (2-chloroethoxy) ethanol (42.2 μL, 0.400 mmol), compound (I-1) (118.7 mg, 0.480 mmol) Trifluoromethanesulfonic acid (3.51 μL, 0.0400 mmol) and 1,4-dioxane (1.33 mL) were added and the mixture was stirred at room temperature under a nitrogen atmosphere for 4 hours. After completion of the reaction, the reaction solution was added to a saturated aqueous solution of sodium bicarbonate, extracted twice with ethyl acetate (10 mL), and washed with saturated brine (20 mL). After washing the obtained organic layer with sodium sulfate, ethyl acetate was distilled off, and the residue was separated and purified by silica gel column chromatography to obtain benzyl 2- (2-chloroethoxy) ethyl ether (76.9 mg, yield 90 %) Was obtained.

Reference： [1]Current Patent Assignee: KANAZAWA UNIVERSITY - JP2017/81832, 2017, A Location in patent: Paragraph 0127; 0129-0131

63
[ 17876-99-2 ]
[ 75-65-0 ]
[ 6669-13-2 ]
[ 103-05-9 ]
[ 103-29-7 ]
[ 100-51-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 16 %Chromat. 2: 10 %Chromat. 3: 9 %Chromat. 4: 5 %Chromat.	In water for 15h; Irradiation;

Reference： [1]Pedroli, Chiara; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio [Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6592 - 6603]

64
[ 1833-42-7 ]
[ 75-65-0 ]
[ 6669-13-2 ]
[ 770-09-2 ]
[ 103-05-9 ]
C₁₄H₂₄OSi [ No CAS ]
[ 101145-03-3 ]
[ 100-51-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 21 %Chromat. 2: 18 %Chromat. 3: 16 %Chromat. 4: 13 %Chromat. 5: 10 %Chromat. 6: 8 %Chromat.	In water for 15h; Irradiation;

Reference： [1]Pedroli, Chiara; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio [Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6592 - 6603]

65
[ 68307-67-5 ]
[ 75-65-0 ]
[ 6669-13-2 ]
[ 770-09-2 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 20 %Chromat. 2: 12 %Chromat. 3: 8 %Chromat.	In water for 15h; Irradiation;

Reference： [1]Pedroli, Chiara; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio [Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6592 - 6603]

66
[ 103-05-9 ]
C₁₂H₁₁BrO [ No CAS ]
C₂₃H₂₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 15.5h;	28 EXAMPLE 28 2-NAPOM Protection of Alcohol Using 2-NAPOMBr EXAMPLE 28 2-NAPOM Protection of Alcohol Using 2-NAPOMBr Ethyldiisopropylamine (0.513 mL, 3.00 mmol) and 2-NAPOM bromide (377 mg, 1.50 mmol) were added to a toluene (1 mL) solution of the alcohol 3a (82.1 mg, 0.500 mmol), and the mixture was stirred at room temperature for 15.5 hours. The mixture was cooled to 0° C. and diluted with ether, and then water was added to stop the reaction. The obtained mixture was subjected to extraction with ether three times, and the organic phases were combined, washed with a saturated potassium hydrogen sulfate aqueous solution and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=50/1→30/1) to obtain the NAPOM ether 3b (125 mg, 0.374 mmol, 75%) as a colorless oily material and the raw material 3a (8.6 mg, 0.0524 mmol, 10%) as a colorless oily material.

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY - US2017/305809, 2017, A1 Location in patent: Paragraph 0076

67
[ 591-50-4 ]
[ 115-18-4 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetramethylammonium formiate; triphenylphosphine In water; N,N-dimethyl-formamide at 80℃; for 16h; regioselective reaction;

Reference： [1]Gurak, John A.; Engle, Keary M. [ACS Catalysis, 2018, vol. 8, # 10, p. 8987 - 8992]

68
[ 103-25-3 ]
[ 74-88-4 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: methyl iodide With magnesium; ethylene dibromide for 1h; Inert atmosphere; Reflux; Stage #2: 3-phenylpropanoic acid methyl ester at 20℃; for 1h; Inert atmosphere;	3 Example 3 General procedure: The MeMgI solution prepared in Example 1 (in terms of 30 mmol) was added to the 4-methyltetrahydropyran solution of the aldehyde compound, the ketone compound, and the ester compound shown in Table 2 and reacted at room temperature for 1 hour. The Grignard reaction product shown was quantified with GC. The reaction results are shown in Table 2.

Reference： [1]Current Patent Assignee: KURARAY CO LTD - JP2015/17073, 2015, A Location in patent: Paragraph 0033; 0034

69
[ 103-05-9 ]
[ 530-62-1 ]
C₁₂H₁₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 4-phenyl-2-methyl-2-butanol; 1,1'-carbonyldiimidazole In toluene at 60℃; Stage #2: With 1H-imidazole; hydroxylamine hydrochloride In toluene

Reference： [1]Guo, Qihang; Ren, Xiang; Lu, Zhan [Organic Letters, 2019, vol. 21, # 4, p. 880 - 884]

70
[ 103-05-9 ]
4-tert-butyl-6-(p-methoxybenzyloxy)-1-propargyl-1,3,5-triazin-2(1H)-one [ No CAS ]
[ 1402544-07-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrabutylammonium p-toluenesulfonate In 1,4-dioxane; nitromethane at 50℃; for 7h;

Reference： [1]Fujita, Hikaru; Terasaki, Hiromitsu; Kakuyama, Satoshi; Hioki, Kazuhito; Kunishima, Munetaka [Organic Letters, 2019]

71
[ 463-51-4 ]
[ 103-05-9 ]
[ 103-07-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	at 60℃; for 20.5h;	2 Example 2: 2-Acetoxy-2-methyl-4-phenylbutane 2-Methyl-4-phenylbutan-2-ol (137.6 g; 0.84 mol) was initially charged as a melt at 60°C (melting point: 24-25°C) and reacted with ketene as described above. Conversion was complete after 20.5 h. The product was purified by fractional distillation (143.5 g; 83%).

Reference： [1]Current Patent Assignee: BASF SE - WO2019/121453, 2019, A1 Location in patent: Page/Page column 19

72
[ 5781-53-3 ]
[ 103-05-9 ]
methyl (2-methyl-4-phenylbutan-2-yl) oxalate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With dmap; triethylamine In tetrahydrofuran at 0 - 25℃; for 5h; Inert atmosphere;
79%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 18h;

Reference： [1]Chen, Changzhou; Gong, Hegui; Lei, Chuanhu; Ma, Guobin; Talukdar, Sangita; Zhao, Xinluo [Chemical Communications, 2020, vol. 56, # 70, p. 10219 - 10222]
[2]Friese, Florian W.; Studer, Armido [Angewandte Chemie - International Edition, 2019, vol. 58, # 28, p. 9561 - 9564][Angew. Chem., 2019, vol. 131, p. 9661 - 9665,5]

73
[ 103-05-9 ]
[ 4755-77-5 ]
ethyl 2-(2-methyl-4-phenylbutan-2-yl)oxy-2-oxoacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;
78%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;

Reference： [1]Amos, Stephanie G. E.; Cavalli, Diana; Le Vaillant, Franck; Waser, Jerome [Angewandte Chemie - International Edition, 2021, vol. 60, # 44, p. 23827 - 23834][Angew. Chem., 2021, vol. 133, # 44, p. 24020 - 24027]
[2]Aguilar Troyano, Francisco José; Ballaschk, Frederic; Jaschinski, Marcel; Özkaya, Yasemin; Gómez-Suárez, Adrián [Chemistry - A European Journal, 2019, vol. 25, # 62, p. 14054 - 14058]

74
4-(3-hydroxy-3-methylbutyl)phenyl dimethylsulfamate [ No CAS ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium phosphate; 4,5-dimethyl-1,3-bis-(2,4,6-trimethylphenyl)-3H-imidazol-1-ium chloride; C₄₆H₃₉ClNiP₂; isopropyl alcohol In toluene at 110℃; for 15.15h;	Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates; General Procedure General procedure: A reaction tube was charged with L2 (11.5 mg, 0.03 mmol), Ni(1-naph)Cl(PPh3)2 (11.2 mg, 0.015 mmol), and K3PO4 (212 mg, 1.0mmol). After the addition of toluene (1.0 mL), the mixture was stirredfor 15 min at 80 °C. Then, aryl sulfamate 1 (0.5 mmol) and 2-propanol(0.1 mL) were added at rt. The reaction mixture was stirred at 80 °Cfor 15 h. After the addition of H2O (5 mL) at rt, the resulting mixturewas extracted with EtOAc (3 × 10 mL), and the combined organic layerswere dried (Na2SO4). Concentration and purification through silicagel column chromatography gave the desired product 2

Reference： [1]Matsuo, Kasumi; Kuriyama, Masami; Yamamoto, Kosuke; Demizu, Yosuke; Nishida, Koyo; Onomura, Osamu [Synthesis, 2021, vol. 53, # 23, p. 4449 - 4460]

75
[ 558-30-5 ]
[ 87100-28-5 ]
[ 103-05-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: pinacol benzylboronate With sec.-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-methyl-1,2-epoxypropane With copper(l) iodide In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Inert atmosphere; regiospecific reaction;	General Procedure of Benzyl Addition to Epoxides General procedure: Two 25 mL round bottom flasks, both with magnetic stir bars, were flame dried under vacuum. Copper(I) iodide (CuI) (4.8 mg, 0.025, mmol, 0.050 eq) was added to one of the flasks. Both flasks were covered with new septum, sealed with parafilm, and purged three times with argon gas. Distilled benzyl boronic pinacol ester (BnBpin) (280 μL, 1.25 mmol, 2.5 eq) and 5 mL of dry THF were added to the empty flask. Both flasks were cooled to -78°C in an ice bath and s-BuLi in hexanes (1.0 mmol, 2.0 eq) was added to the BnBpin to make the nucleophilic boronate complex. The reaction stirred for 30 minutes before the boronate were transferred via syringe to the flask containing CuI. Immediately after the nucleophile transfer, the epoxide (0.50 mmol, 1.0 eq) was added and the reaction was allowed to stir for 15 minutes at -78 °C. The reaction was then removed from the cold bath and left to stir for 2 hours and 45 minutes. At completion, the reaction was quenched with 0.3 mL of sat. NH4Cl (aq). The reaction mixture was then worked up (10 mL sat. NH4Cl (aq), 3 * 10 mL EtOAc,10 mL brine), dried with Na2SO4, concentrated under reduced pressure. An internal standard (pyridine (41 μL) was added, and the unpurified reaction mixture was characterized via 1H NMR. The product was then purified by column chromatography.

Reference： [1]Gierszal, Sophia G.; Barker, Timothy J. [Tetrahedron Letters, 2021, vol. 82]

76
[ 103-05-9 ]
[ 91-60-1 ]
(2-m-4-phenylbutan-2-yl)(naphthalen-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

77
[ 371-42-6 ]
[ 103-05-9 ]
(4-fluorophenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated. 2. Experimental Details (4-Fluorophenyl)(2-methyl-4-phenylbutan-2-yl)sulfane (3).The title compound was prepared according the general procedure. After purification by a flash column chromatography (SiO2: petroleum ether), the title compound was isolated in 97% yield (79.9 mg, 0.291 mmol) as a pale yellow oil. 1H NMR (500 MHz, CDCl3): δ 7.54-7.48 (m, 2H), 7.28 (dd, J = 8.7, 6.6 Hz, 2H), 7.21-7.16 (m, 3H), 7.04-6.98 (m, 2H), 2.83-2.78 (m, 2H), 1.78-1.73 (m, 2H), 1.29 (s, 6H).13C NMR(126 MHz, CDCl3): δ 164.40, 162.42, 142.31, 139.37, 139.31, 128.45, 128.34, 127.55, 127.52, 125.84, 115.76, 115.59, 49.16, 44.08, 31.31, 28.73.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

78
[ 6320-03-2 ]
[ 103-05-9 ]
(2-chlorophenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

79
[ 2037-31-2 ]
[ 103-05-9 ]
(3-chlorophenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

80
[ 103-05-9 ]
[ 106-53-6 ]
(4-bromophenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

81
[ 103-05-9 ]
[ 36801-01-1 ]
4-((2-methyl-4-phenylbutan-2-yl)thio)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

82
[ 5858-17-3 ]
[ 103-05-9 ]
(3,4-dichlorophenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

83
[ 103-05-9 ]
[ 130783-02-7 ]
(3,5-bis(trifluoromethyl)phenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

84
[ 103-05-9 ]
[ 2396-68-1 ]
(4-(tert-butyl)phenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

85
[ 696-63-9 ]
[ 103-05-9 ]
(4-methoxyphenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

86
[ 700-96-9 ]
[ 103-05-9 ]
(3,4-dimethoxyphenyl)(2-methyl-4-phenylbutan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(II) bis(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at 70℃; for 12h;Schlenk technique;	General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Tetrahedron Letters,2022,vol. 89

87
[ 103-05-9 ]
[ 147-93-3 ]
2-((2-methyl-4-phenylbutan-2-yl)thio)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique; chemoselective reaction;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

88
[ 637-89-8 ]
[ 103-05-9 ]
4-((2-methyl-4-phenylbutan-2-yl)thio)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique; chemoselective reaction;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

89
[ 103-05-9 ]
[ 1126-81-4 ]
N-(4-((2-methyl-4-phenylbutan-2-yl)thio)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 60℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	103-05-9	MDL No. :	MFCD00004472
Formula :	C₁₁H₁₆O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YXVSKJDFNJFXAJ-UHFFFAOYSA-N
M.W :	164.24	Pubchem ID :	7632
Synonyms :

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	1760
Hazard Statements:	H318	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 103-05-9 ] {[proInfo.proName]}

Quality Control of [ 103-05-9 ]

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Application In Synthesis of [ 103-05-9 ]

[ 103-05-9 ] Synthesis Path-Downstream 1~89

Precautionary Statements-General

Prevention

Response

Storage

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Health hazards

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Inquiry