Diiodomethane → 1beta,2beta-Methylene-5-androstene-3beta,17beta-diol

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Reaction Steps

To a stirred solution consisting of 1,5-androstadiene-3β,17β-diol in a mixture of dry ether and glyme is added zinc-copper couple and methylene iodide. This mixture is refluxed for approximately 4 hours, cooled to room temperature, diluted with ether and filtered. The filtrate is washed with aqueous sodium chloride, water and dried over anhydrous magnesium sulfate. The ether is removed under reduced pressure and the residue is crystallized from an acetone-hexane solution to yield 1β,2β-methylene-5-androstene-3β,17β-diol.

Provenance & Evidence