Ammonium Chloride → 2-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethanol

反応式

[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH:19][CH2:20][CH2:21][C:22]1([CH2:28][CH2:29][OH:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[Cl-].[NH4+]>C(Cl)Cl>[O:19]([CH2:20][CH2:21][C:22]1([CH2:28][CH2:29][OH:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

実験手順

tert-Butylchlorodiphenylsilane (34.4 mL, 0.132 mol) was added dropwise to a solution of 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol (21.7 g, 0.126 mol) in methylene chloride (280 mL) while cooling on ice. After stirring the mixture for 14 hours at room temperature, 25% aqueous ammonium chloride (300 mL) was added and extraction was performed. The organic layer was washed with saturated aqueous sodium chloride, and then the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (500 g Merck Art. 9385, hexane:ethyl acetate=4:1) to obtain the title compound as a colorless oil (36.8 g) (2 steps, 60% yield).