Acetic Anhydride → HCID 70046766, compound

Participants

Reaction Steps

A solution of 7.9 g of 3β,11β-dihydroxy-15β,16β-methyleneandrost-5-en-17-one in 39.5 ml of pyridine and 39.5 ml of acetic anhydride is left to stand at room temperature for 5 hours, diluted with 800 ml of ice-water and, after standing for 1 hour, extracted with ethyl acetate. The organic phase is washed in succession with saturated sodium chloride solution, ice-cold dilute hydrochloric acid, ice-cold dilute sodium hydroxide solution and again with saturated sodium chloride solution, dried, and concentrated under a water-jet vacuum. Chromatography of the crude product over 30 times the amount by weight of silica gel and elution with a mixture of methylene chloride/acetone (98:2) yield 3β-acetoxy-11β-hydroxy-15β,16β-methyleneandrost-5-en-17-one which, after being dissolved and recrystallised once from methylene chloride/ether/petroleum ether, melts at 209°-211°.

Provenance & Evidence