Sodium Chloride → 3,3-(Ethylenedioxy)-11-[4-(3-pyridyl)phenyl]-5-estren-17-one

Participants

Reaction Conditions

Reaction Steps

4.92 g (9.1 mmol) of 3,3-(ethylenedioxy)-11β-(4-trifluoromethylsulfonyloxyphenyl)-5-estren-17-one is dissolved in a mixture of 80 ml of toluene and 35 ml of ethanol and mixed in succession with 0.53 g of palladiumtetrakistriphenylphosphine, 0.77 g of lithium chloride, 11 ml of 2 molar sodium carbonate solution and 1.47 g (10 mmol) of diethyl(3-pyridyl)borane. The reaction mixture is then stirred for one hour at 110° 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, washed on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane. 3.55 g of 3,3-(ethylenedioxy)-11-[4-(3-pyridyl)phenyl]-5-estren-17-one and 382 mg of 3,3-(ethylenedioxy)-11-(4-ethylphenyl)-5-estren-17-one are obtained as white foams.

Provenance & Evidence