p-Toluenesulfenyl chloride → HCID 70564755, compound

Participants

Reaction Steps

A solution of 900 mg of 9-fluoro-11β-hydroxy-17-(methylthio)androsta-1,4,16-trien-3-one in 900 ml of dichloromethane is stirred with 500 mg of p-toluenesulfenyl chloride at room temperature under a nitrogen atmosphere for about 16 hours. The resulting solution is washed with water, dried over anhydrous Na2SO4 and evaporated in vacuo to give 1.3 g of a solid, which is dissolved in chloroform-hexane (3:2) and chromatographed on a 50 g-silica gel column. Elution with chloroform-hexane (3:2) gives 930 mg of a tlc-homogenous material. Two crystallizations from acetone-hexane give 400 mg of an analytical specimen of the title compound, melting point 205°-206° C.

Provenance & Evidence