Water → HCID 68949346, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 10.34 g of lithium bromide and 53.2 g of copper(II) bromide in 280 ml of acetonitrile is added in drops to a solution of 47 g of 7α-(5-chloropentyl)-11β-fluoro-estr-4-ene-3,17-dione in 470 ml of acetonitrile at a bath temperature of 80° C. After 20 ml is added, the bleaching of the solution is awaited, and the remainder of the solution is added in 12 minutes and then stirred for 5 more minutes at a bath temperature of 80° C. Then, it is cooled to 0° C., mixed with sodium bicarbonate solution, added to water, extracted 4 times with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 25.3 g of 7α-(5-chloropentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained. [α]D22=+115.4° (c=0.5% in chloroform).

Provenance & Evidence