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

関与物質

反応条件

反応手順

To a solution of 156 mg (1.00 mmol) of methyl 2,2-dimethyl-3-formylcyclopropane carboxylate and 0.226 ml (2.00 mmol) of 1,1,1-trichlorotrifluoroethane in 1 ml of dimethylformamide (DMF), 98 mg (1.50 mmol) of zinc powder was added at 0° C., and the mixture was stirred at 0° C. for 20 minutes, and at 50° C. for 7 hours. Then, 1 ml of a saturated ammonium chloride aqueous solution was added, and the mixture was extracted with diethyl ether (2 ml×5 times). The extract was dried over anhydrous magnesium sulfate, then filtered and concentrated under reduced pressure. The product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/2) to obtain 232 mg of methyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate (a mixture of two stereoisomers in a ratio of 55:45) as a colorless oil.

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