反应详情

11.5 ml of perfluorobutane-1-sulfonic acid fluoride was added in drops at 0° C. to a solution of 13.08 g of 11α-hydroxy-7α-methyl-estr-4-ene-3,17-dione (produced by means of microbiological synthesis according to the invention [Part A]) in 250 ml of toluene and 18.2 ml of 1,8-diazabicyclo[5,4,0]undec-7-ene. After 1 hour, it was neutralized with 2 M hydrochloric acid, added to water, extracted four times with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated by evaporation in a vacuum. After the crude product was chromatographed on silica gel with a hexane/ethyl acetate gradient, 8.7 g of 11β-fluoro-7α-methyl-estr-4-ene-3,17-dione was obtained. Melting point: 101.4° C., [α]D: +135.8° (CHCl3).

1. customproduced by means of microbiological synthesis
2. extractionextracted four times with ethyl acetate
3. washwashed with saturated sodium chloride solution
4. customdried
5. concentrationconcentrated by evaporation in a vacuum
6. customAfter the crude product was chromatographed on silica gel with a hexane/ethyl acetate gradient