Toluene → HCID 9821134, compound

Participants

Reaction Conditions

Reaction Steps

17,17-bis-(ethylenedioxy)-11-trifluoromethylsulfonyloxy-5,11-estradiene is dissolved in a mixture of 31 ml of toluene and 14 ml of ethanol and mixed in succession with 0.2 g of palladiumtetrakistriphenylphosphine, 0.29 g of lithium chloride, 4.4 ml of 2 molar sodium carbonate solution and 0.5 g (3.7 mmol) of 4-methylphenylboronic acid. The reaction mixture is then stirred for 1 hour 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. 1.28 g of the title compound is obtained as white foam.

Provenance & Evidence