Benzene → 4-Methoxy-6-methylenandrost-4-ene-3,17-dione

Participants

Reaction Steps

To a solution of 4-hydroxy-6-methylenandrost-4-ene-3,17-dione (0.315 g, 1 mmole) in benzene (10 ml) potassium tert-butoxide (0.224 g, 2 mmole) is added and the mixture heated to reflux for 30 minutes. After cooling, iodomethane (0.710 g, 5 mmole) is added and the mixture boiled for a further 2 hours. Then the organic solution is washed with water, dried and evaporated in vacuum. Flash column chromatography of the residue on silica gel using n-hexane/ethyl acetate 60:40 affords 0.247 g (75% yield) of the title compound, m.p. 196°-198° C.

Provenance & Evidence