Diethoxymethane → HCID 66852514, compound

Participants

Reaction Steps

A mixture of sodium acetate (1 g), absolute chloroform (30 ml), formaldehyde diethyl acetal (30 ml, 0.24 mol), phosphoryl chloride (3.8 ml, 0.04 mol), and 1,2β-methylenandrost-4-en-3,17-dione (0.806 g, 2.7 mmol) is stirred at reflux for about 5 hours, i.e. until the starting material has disappeared. The suspension is allowed to cool and under vigorous stirring a saturated sodium carbonate solution is added dropwise until the pH of the aqueous layer becomes alkaline (ca. 1 hour). The organic layer is separated, neutralized with water, and dried with sodium sulfate. After concentration under reduced pressure the oily residue is purified by chromatography on silica gel using hexane/ethyl acetate as eluent. Thus the pure 6-methylen-1,2β-methylenandrost-4-ene-3,17-dione is obtained in 60% yield (0.194 g).

Provenance & Evidence