4-Toluenesulfonyl chloride → 3beta-Toluene-p-sulphonyloxy-5alpha-pregn-16-ene-11,20-dione

Participants

Reaction Steps

A solution of 3β-hydroxy-5α-pregn-16-ene-11,20-dione (39.6 g) in dry pyridine (165 ml.) was treated with toluene-p-sulphonyl chloride (43.9 g.) to give 3β-toluene-p-sulphonyloxy-5α-pregn-16-ene-11,20-dione (56.7 g.) m.p. 147°-151°. A portion (10.7 g.) of this material was crystallised from ethyl acetate-petrol to give the pure toluenesulphonate (9.2 g.) as plates m.p. 154°-155°, [α]D + 42.8° (c 1.2).

Provenance & Evidence