反应详情

3.3 ml of a 1.6 molar solution of butyllithium in hexane is slowly instilled in a solution of 423 μl of thiophene in 8 ml of tetrahydrofuran at room temperature under protective gas. After 30 more minutes of stirring, 872 mg of dry zinc(II) chloride, dissolved in 5 ml of diethyl ether, is added to the reaction mixture and stirred for one hour at room temperature. The thus produced 2-thienylzinc chloride solution is instilled in a solution of 480 mg of 3,3-(ethylenedioxy)-11β-(4-trifluoromethylsulfonyloxyphenyl)-5-estren-17-one and 51 mg of tetrakistriphenylphosphinepalladium in 10 ml of tetrahydrofuran. The reaction mixture is stirred for eight hours under reflux, cooled to room temperature and mixed with saturated ammonium chloride solution. The aqueous phase is extracted three times with ethyl acetate. The organic phases are washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. Chromatography of the residue on silica gel with a mixture of ethyl acetate/hexane yields 380 mg of the title compound as white foam.

1. additionis added to the reaction mixture
2. stirringstirred for one hour at room temperature
3. stirringThe reaction mixture is stirred for eight hours
4. temperatureunder reflux
5. extractionThe aqueous phase is extracted three times with ethyl acetate
6. washThe organic phases are washed with saturated sodium chloride solution
7. customdried on sodium sulfate
8. concentrationconcentrated by evaporation in a vacuum
9. additionChromatography of the residue on silica gel with a mixture of ethyl acetate/hexane