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

Participants

Reaction Steps

4.6 ml of perfluorobutane-1-sulfonic acid fluoride was added in drops at 0° C. to 5.0 g of 11β-hydroxy-estr-4-ene-3,17-dione (A) [J. de Flines et al., Recl. Trav. Chim. Pays-Bas, Vol. 82, pages 129 ff., (1963)) in 100 ml of toluene and 7.3 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene. After 30 minutes, the solution was diluted with ethyl acetate, washed with saturated sodium chloride solution and dried. Then, it was concentrated by evaporation in a vacuum. After the crude product was chromatographed on silica gel with a hexane-ethyl acetate gradient, 3.8 g of 11β-fluoro-estr-4-ene-3,17-dione (A′) with a melting point of 173-174° C. was obtained.

Provenance & Evidence