Ammonium Chloride → 1-(4-Benzyloxyphenyl)-1-(4-tert-butyldimethylsiloxy-phenyl)-2-phenyl-butan-1-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 19.32 g of (4-bromophenoxy)-tert-butyldimethylsilane in 50 ml of tetrahydrofuran is added in drops to a suspension of 1.58 g of magnesium chips in 100 ml of tetrahydrofuran at 80° C. bath temperature, and it is refluxed for 1 hour. Then, it is cooled to 0° C., and 6.0 g of 1-(4-benzyloxyphenyl)-2-phenyl-butan-1-one [D. W. Robertson; J. A. Katzenellenbogen; D. -J. Ellen; A. Rorke; B. S. Katzenellenbogen, J. Steroid Biochem., 1982, 16, 1-13] is added, and it is stirred for 24 more hours at room temperature. For working-up, 60 ml of saturated ammonium chloride solution is added, diluted with ethyl acetate, washed neutral with water, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 9.1 g of 1-(4-benzyloxyphenyl)-1-(4-tert-butyldimethylsiloxy-phenyl)-2-phenyl-butan-1-ol is obtained as oil.

Provenance & Evidence