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

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Reaction Conditions

Reaction Steps

To a solution of 174 mg (1.02 mmol) of ethyl 2,2-dimethyl-3-formylcyclopropanecarboxylate in 1 ml of DMF, 96 mg (1.47 mmol) of zinc powder and 0.356 ml (3.00 mmol) of 1,1,1-trichlorotrifluoroethane were added, and the mixture was stirred at 0° C. for 2 hours and at 50° C. for 10 hours. Then, 2 ml of a saturated ammonium chloride aqueous solution was added thereto, and the mixture was extracted with diethyl ether (2 ml×3 times). The ethereal 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=1/1) to obtain 188 mg of ethyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3trifluoropropyl)cyclopropanecarboxylate (a mixture of two stereoisomers in a ratio of 94:46).

Provenance & Evidence