Abstract
4-En-3-oxo-steroid is converted into 4-chloro-4-en-3-oxo-steroid by treatment with sulfuryl chloride in pyridine. Testosterone acetate (Va), testosterone propionate (VII), progesterone (Vb), cholest-4-en-3-one (Vc), and androst-4-ene-3, 17-dione (X) are also converted respectively into the corresponding 4-chloro-4-en-3-oxo-steroids, (VIa) (87.6%), (VIII) (82.7%), (VIb) (73.9%), (VIc) (65.9%), and (XI) (71.4%). (XI) was also obtained from 4-chlorotestosterone (IX) by oxidation with chromium trioxide in acetic acid or chromium trioxide-pyridine complex. (IX) was prepared by the saponification of (VIII) with hydrochloric acid.
