Water → Methyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate

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To a solution of 156 mg (1.00 mmol) of methyl 2,2-dimethyl-3-formylcyclopropanecarboxylate in 1 ml of DMF, 78 mg (1.19 mmol) of zinc powder and 0.177 ml (1.50 mmol) of 1,1,1-trichlorotrifluoroethane were added at 0° C., and the mixture was stirred at 0° C. for 30 minutes and at 50° C. for 10 hours. Then, 0.5 ml of acetic anhydride was added at room temperature, and the mixture was stirred for 10 minutes. After an addition of 2 ml of water, the mixture was extracted with diethyl ether (2 ml×5 times). The extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=2/3) to isolate 122 mg (35%) of methyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate and 133 mg (43%) of methyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate.

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