[CH:1]1([CH2:9][OH:10])[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[C:11]([Si:15]([CH3:18])([CH3:17])Cl)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1.[Br-].[Li+]>CN(C)C=O>[Si:15]([O:8][CH2:7][CH:4]1[CH2:5][CH2:6][CH:1]([CH2:9][OH:10])[CH2:2][CH2:3]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:18])[CH3:17]To a solution of cyclohexane-1,4-dimethanol (10.0 g) in N,N-dimethylformamide (100 mL) were added successively tert-butyldimethylchlorosilane (8.9 g) and imidazole (9.5 g), followed by stirring the reaction mixture at room temperature for 16 hours. To the reaction mixture were added ice and saturated aqueous lithium bromide solution, followed by extraction with diethyl ether. The organic layer was washed with saturated aqueous lithium bromide solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:9 to 2:3) to give [4-(tert-butyldimethylsilanyloxymethyl)-cyclohexyl]-methano 1 (8.7 g).
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