Hexane → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-oxopregna-5,7,16-triene

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Reaction Steps

(1α,3β)-1,3-Bis((tert-butyl(dimethyl)silyl)oxy)androsta-5,7,16-trien-17-yl trifluoromethanesulfonate (40.3 g) was dissolved in dimethylacetamide (203 ml), followed by addition of tetrakis(triphenylphosphine)palladium(0) (703 mg). The resulting mixture was placed under reduced pressure and then placed in a carbon monoxide atmosphere. This procedure was further repeated twice. A 0.98 M hexane solution of dimethylaluminum chloride (74.4 ml) was added to the mixture at room temperature and then stirred at room temperature for 20 minutes. After heating to 58° C. and stirring for 2 hours, water was added to the reaction mixture, which was then extracted with hexane/ethyl acetate=1/1. The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the titled compound (34.0 g, yield 100%).

Provenance & Evidence