m-Chloroperbenzoic acid → HCID 86733314, compound

Participants

Reaction Steps

16-Methyl-5α-pregna-2,16-diene-11,20-dione (800 mg.) in methylene chloride (50 ml.) was treated with m-chloroperbenzoic acid (85%; 535 mg.), and the solution was left to stand at room temperature overnight. More methylene chloride (50 ml.) was added and the solution washed with potassium bicarbonate solution (5%, 100 ml.) and with water (100 ml.), dried over sodium sulphate and evaporated to a crystalline solid (~ 1g.) which was purified by preparative TLC in ethyl acetate/petrol, 1/1 run twice. The main band yielded a white solid (650 mg.) which was recrystallised from acetone/ petrol to give title compound (515 mg.) as white crystals, m.p. 155°-157°, [α]D + 57.8° (c 0.9), λmax. (EtOH) 246.5 nm (ε 9150).

Provenance & Evidence