Sodium Chloride → 3,3-(Ethylenedioxy)-11beta-[4'-(methylthio)[1,1'-biphenyl]-4-yl]-5-estren-17-one

Participants

Reaction Conditions

Reaction Steps

1.73 g of 3,3-(ethylenedioxy)-11β-(4-trifluoromethylsulfonyloxyphenyl)-5-estren-17-one is dissolved in a mixture of 17 ml of toluene and 5 ml of ethanol and mixed in succession with 37 mg of palladiumtetrakistriphenylphosphine, 0.28 mg of lithium chloride, 4 ml of 2 m sodium carbonate solution and 0.7 g of [4-(methylthio)phenyl]boronic acid. The reaction mixture is then stirred for 6 hours at 95° C., cooled to room temperature and mixed with saturated sodium chloride solution. The organic phase is separated, washed in succession with 5% sodium hydroxide solution and water, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane. 1.65 g of the title compound is obtained as white foam.

Provenance & Evidence