2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 16alpha-Fluoro-1,6alpha-dimethyl-7-methylenandrosta-1,4-diene-3,17-dione

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Reaction Steps

A mixture of 16α-fluoro-1β,6α-dimethyl-7-methylenandrost-4-ene-3,17-dione (344 mg) and dichlorodicyanobenzoquinone (363 mg) in dioxane (20 ml) is refluxed for about 15 hours. Then the resulting suspension is cooled, the precipitate filtered off and the filtrate evaporated in vacuo. The residue is dissolved in ethyl acetate, the organic layer washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude product is chromatographed on silica gel using hexane/ethyl acetate as eluant to yield 16α-fluoro-1,6α-dimethyl-7-methylenandrosta-1,4-diene-3,17-dione (222 mg).

Provenance & Evidence