[CH2:1]([O:8][C:9]([CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCCCCC.C(OCC)(=O)C>CN(C)C=O.O.CCCCCC>[CH2:1]([O:8][C:9]([CH2:11][C@H:12]1[CH2:13][CH2:14][C@H:15]([O:18][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:16][CH2:17]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
To a solution of trans-4-benzyloxycarbonylmethyl-1-hydroxycyclohexane (2.20 g, 8.86 mmol) in dimethylformamide (31 mL) were added imidazole (953 mg, 14.0 mmol) and t-butyldimethylsilyl chloride (1.60 g, 10.6 mmol) at room temperature, and the mixture was stirred at 60° C. for 3 h. The reaction mixture was diluted with water (70 mL) and hexane (200 mL) with stirring under ice cooling to separate the phases. The aqueous layer was extracted again with hexane, and the combined organic layer was concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 50:1) to give 2.96 g of trans-4-benzyloxycarbonylmethyl-1-t-butyldimethylsilyloxycyclohexane as oil (yield: 92%).
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