Perfluoro-1-butanesulfonyl fluoride → 11beta-Fluorooestr-4-ene-3,17-dione

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Reaction Steps

4.6 ml of perfluorobutane-1-sulfonic acid fluoride is added in drops to 5.0 g of 11α-hydroxy-estr-4-ene-3,17-dione in 100 ml of toluene and 7.3 mnl of 1,8-diazabicyclo[5,4,0]undec-7-ene at 20° C. After 30 minutes, the solution is diluted with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient, 3.8 g of 11β-fluoro-estr-4-ene-3,17-dione with a melting point of 173-174° C. is obtained.

Provenance & Evidence