Diethyl cyclopropane-1,1-dicarboxylate → Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

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Reaction Steps

In accordance with the method described in the document (Tetrahedron Letters, 40, 5467 (1988)), a solution of 720 mg of 1-hydroxymethyl-cyclopropane carboxylic acid ethyl ester obtained from 1,1-cyclopropane dicarboxylic acid diethyl ester in 10 mL of dichloromethane was added with 1.05 mL of triethylamine and 0.5 mL of methanesulfonyl chloride under ice cooling, and stirred at this temperature for 2 hours. After adding water, the reaction solution was extracted with ethyl acetate. The organic layer was washed successively with 1N hydrochloric acid, saturated brine, saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, to afford 1.04 g of the title compound as a pale yellow oil.

Provenance & Evidence