Phosphorus oxychloride → HCID 54386943, compound

Participants

Reaction Steps

A suspension of 1.0 g of sodium acetate in 30 ml of chloroform, 30 ml of formaldehyde diethylacetal, and 3.8 ml of phosphorus oxychloride is combined with 1.0 g of 5-androstene-7,17-dione and refluxed for 61/2 hours. Under agitation, a saturated soda solution is then added dropwise until alkaline reaction occurs in the aqueous phase. The organic phase is separated, washed with water, dried over sodium sulfate, and concentrated under vacuum. The crude product is purified on 200 g of silica gel with a hexane/ethyl acetate gradient (0-50% ethyl acetate), thus isolating 840 mg of 4-methylene-5-androstene-7,17-dione, mp 131.5°-132° C.

Provenance & Evidence