(Aminomethyl)phosphonic acid → Prop-2-en-1-yl 7-oxabicyclo[4.1.0]heptane-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A three neck flask of 500 mL equipped with a reflux condenser, a thermometer, a stirring device, a dropping funnel and an oil bath was charged with 100.0 g of allyl 3-cyclohexene-1-carboxylate, 2.34 g of methyl hydrogensulfate trioctylammonium, 3.96 g of sodium tungstate dihydrate and 0.45 g of aminomethylphosphonic acid. The flask was heated on the oil bath maintained at 90° C., and 80 ml of 30% aqueous hydrogen peroxide was dropwise added thereto through the dropping funnel in 180 minutes to ripen the solution as it was for 4 hours. The flask was cooled on an ice bath, and surplus hydrogen peroxide was removed by 300 ml of a saturated sodium thiosulfate aqueous solution. Then, the solution was extracted twice with 200 ml of ethyl acetate. The ethyl acetate solution thus obtained was dried on anhydrous sodium sulfate for a night, and ethyl acetate which was the solvent was removed by means of a rotary evaporator. Then, the residue was refined by a silica gel chromatography filled with 25% hydrous silica gel to obtain 79.6 g of allyl 3,4-epoxycyclohexane-1-carboxylate.

Provenance & Evidence