Sulfuric Acid → 11beta-Fluoro-17beta-hydroxy-7alpha-methylestr-4-en-3-one

Participants

Reaction Conditions

Reaction Steps

A solution of 8.7 g of 11β-fluoro-7α-methyl-estr-4-ene-3,17-dione in 148 ml of tetrahydrofuran was mixed drop by drop at 0° C. with 29.5 ml of 1 M lithium aluminium tri-tert-butoxyhydride in tetrahydrofuran and stirred for 5.5 hours at 0° C. Then, dilute sulfuric acid was added at 0° C., and the reaction solution was added to ice water, extracted three times with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 5.8 g 11β-fluoro-17β-hydroxy-7α-methylestr-4-en-3-one with a melting point of 143-144° C. was obtained. [α]D=+89.9° (CHCl3).

Provenance & Evidence