Water → HCID 54123535, compound

Participants

Reaction Conditions

Reaction Steps

3.1 g (10 mmol) of pregna-1,4,16-trien-20-one is mixed in 25 ml of dioxane with 143.4 mg of CuBr. 9.4 ml (11 mmol) of a 10% solution of trimethyl aluminum in toluene is added to the reaction under nitrogen and stirred for 30 minutes at 20-30° C. For hydrolysis, 0.54 ml of water dissolved in 5 ml of dioxane is added to the reaction. It is stirred for 10 minutes more and the precipitate is filtered off. The precipitate is washed again with a little dioxane. The dioxane solution is concentrated by evaporation on a rotary evaporator and the residue is chromatographed on silica gel with ethyl acetate/hexane as eluent. After concentration by evaporation of the fractions, 2.6 g of 16α-methyl-pregna-1,4-dien-20-one (80% of theory) of a melting point of 175° C. is obtained.

Provenance & Evidence