2-Phenylethanethiol → 17alpha-(beta-Phenylethylthio)-1,4-Androstadiene-3,11-Dione

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Reaction Steps

To 2.25 gm. of sodium metal dissolved in 180 ml. of ethanol is added 8 ml. of β-phenylethyl mercaptan followed by 3 gm. of 17β-methanesulfonyloxy-1,4-androstadiene-3,11-dione. Heat the reaction at reflux for 48 hours. Obtain a residue in a manner similar to that described in Example 1A. Chromatograph the residue on a 300 gm. silica gel column eluting with chloroform/ethyl acetate (2:1). Combine the desired fractions as determined by thin layer chromatography, evaporate and crystallize the resultant residue from ether/hexane to obtain the title compound; m.p. 112°-115° C.

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