C(Cl)Cl.[F:4][CH:5]1[CH:10]([O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8][CH:7]([OH:20])[CH2:6]1.C(N(CC)C(C)C)(C)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(OCC)(=O)C.CCCCCC>[CH3:30][S:31]([O:20][CH:7]1[CH2:8][CH2:9][CH:10]([O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]([F:4])[CH2:6]1)(=[O:33])=[O:32]
A methylene chloride (10 mL) solution of 3-Fluoro-4-(2-phenylethoxy)cyclohexanol (0.450 g, 1.89 mmol) in N,N-diisopropylethylamine (0.688 mL, 3.96 mmol) was cooled in an ice bath under nitrogen. Methanesulfonyl chloride (0.154 mL, 1.98 mmol) was added dropwise to the reaction solution. After 0.5 h the contents of the reaction flask were washed with 5% potassium bisulfate. The aqueous layer was extracted (2×) with methylene chloride and the combined organic portions dried with anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. Flash column chromatography (hexane:ethyl acetate, 60:40) gave 3-Fluoro-4-(2-phenylethoxy)cyclohexyl methanesulfonate as a colorless oil (0.597 g, 100% yield).
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