Methyl iodide → 3Oxo-17beta-(hydroxymethyl)-4-methyl-4-androstene

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Reaction Steps

A mixture of potassium t-butoxide (5 g) in 100 ml t-butanol is heated to reflux. A solution of 3-oxo-17β-(hydroxymethyl)-4-androstene (10 g) in t-butanol is added followed by a solution of methyl iodide (2.7 g) in t-butanol. Heating is continued for 3 hours. The mixture is then cooled, acidified, and extracted with dichloromethane. The dichloromethane solution is washed with brine, dried, and concentrated to yield 3-oxo-17β-(hydroxymethyl)-4-methyl-4-androstene.

Provenance & Evidence