Hydrochloric Acid → 7alpha-(6-Chlorohexyl)-11beta-fluor-3-hydroxy-estra-1,3,5(10)-trien-17-one

Participants

Reaction Conditions

Reaction Steps

28.1 g of copper(II) bromide and 5.4 g of lithium bromide in 105 ml of anhydrous acetonitrile are added at 80° C. to 25.2 g of 7α-(6-chlorohexyl)-11β-fluorooestr-4-ene-3,17-dione in 175 ml of anhydrous acetonitrile. After 15 minutes, the reaction mixture is cooled to 0° C. and 250 ml of saturated sodium hydrogencarbonate solution are added dropwise. The solution is then stirred into 1 litre of water, brought to pH=6 with 2N hydrochloric acid, extracted 3 times with ethyl acetate, washed with sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. Chromatography of the crude product on silica gel using a hexane-ethyl acetate gradient yields 5.7 g of 7α-(6-chlorohexyl)-11β-fluoro-3-hydroxyestra-1,3,5(10)-trien-17-one as a foam.

Provenance & Evidence