C([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)[CH:11]([F:25])[CH2:10]1)C1C=CC=CC=1.CCCCCC>[Pd].C(OCC)(=O)C>[F:25][CH:11]1[CH:12]([O:15][CH2:16][CH2:17][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10]1To an ethyl acetate (100 mL) solution of (−) 2-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethanone (1.44 g, 4.18 mmol) was added 10% palladium on carbon (0.200 g). The resulting mixture was hydrogenated using a balloon. After 20 h the contents of the reaction flask were filtered through celite® and the filtrate evaporated under reduced pressure. Flash column chromatography (hexane:ethyl acetate, 60:40) gave 3-Fluoro-4-(2-phenylethoxy)cyclohexanol as a colorless oil (0.918 g, 92% yield).
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