Sodium Thiosulfate → Benzyl (1R*,3S*,4R)-3,4-epoxycyclohexane-1-carboxylate

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Reaction Steps

Benzyl (±)-3-cyclohexene-1-carboxylate (40 g) was dissolved in dichloromethane (500 ml), and m-chloroperbenzoic acid (86 g) was added under ice cooling to stir the mixture for 2 hours. After a 10% aqueous solution of sodium thiosulfate was added to conduct stirring for 20 minutes, an organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9) to obtain the title compound (23.4 g) and benzyl (1R,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (12.1 g) as colorless oils.

Provenance & Evidence