Ethyl Acetate → 2-(1-Methoxy-cyclopropyl)-2-(4-chlorophenyl)-oxirane

Participants

Reaction Steps

A suspension of 0.82 g (0.0342 mol) of sodium hydride, 7.5 g (0.0342 mol) of trimethylsulphoxonium iodide and 50 ml of dimethyl sulphoxide is initially stirred at room temperature for 30 minutes and then a solution of 6.0 g (0.0285 mol) of 1-methoxy-cyclopropyl 4-chlorophenyl ketone in 10 ml of dimethyl sulphoxide is added at 10° C. After addition is complete, the mixture is warmed to room temperature and stirred for a further 3 hours. 10 ml of ethyl acetate are then added to the reaction mixture and it is stirred for a further 5 minutes. The reaction mixture is poured into ice-water, the resulting mixture is extracted three times with cyclohexane, and the combined organic phases are dried over sodium sulphate and concentrated by stripping off the solvent under reduced pressure. 5.4 g (84% of theory) of 2-(1-methoxy-cyclopropyl)-2-(4-chlorophenyl)-oxirane are obtained in this manner and reacted further without additional purification. ##STR38##

Provenance & Evidence