(11-beta)-17,17-Bis(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4-dien-3-one → 17-Ethylthio-9-fluoro-11beta-hydroxyandrosta-1,4,16-triene-3-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 1.8 g of 17,17-bis(ethylthio)-9-fluoro-11β-hydroxyandrosta-1,4-dien-3-one in 120 ml of diethylbenzene is stirred at 190° C (oil bath temperature) for 1 hour. The solution is cooled to 0° C and the solid that precipitates is filtered. This is redissolved in 1:9 hexane-chloroform and chromatographed on a 60 g-silica gel column. Elution with 1:9 hexane-chloroform gives 1.35 g of a tlc-homogeneous material. Crystallization from chloroform-methanol gives 680 mg of the title compound, melting point 282°-283° C (dec.), with consistent spectral data.

Provenance & Evidence