Pyridine → Carbonic acid 1-chloroethyl ester (1R,2R)-2-methylcyclohexyl ester

Participants

Reaction Steps

To a mixture of 1-chloroethyl chloroformate [CSA No. 50893-53-3] (0.416 mL), pyridine (0.624 mL), and THF (25 mL), (1R,2R)-2-methylcyclohexanol [CSA No. 19043-03-9] (441 mg) dissolved in THF (5 mL) was added at −78° C. After stirring the mixture overnight at room temperature, ethyl acetate (100 mL) and heptane (100 mL) were added to the mixture. The resulting mixture was sequentially washed with 0.5 N hydrochloric acid (50 mL), saturated aqueous sodium hydrogen carbonate solution (50 mL), water (50 mL), and saturated aqueous sodium chloride solution (50 mL), and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure to obtain the captioned compound (482 mg).

Provenance & Evidence