Iodine → 17beta-Acetoxy-2-iodo-1alpha-methyl-androst-4-en-3-one

Participants

Reaction Conditions

Reaction Steps

6.88 g (20 mmol) of 17β-acetoxy-1α-methyl-androst-4-en-3-one and 1.75 g (22 mmol) of CuO in 60 ml of acetic acid are mixed with stirring at room temperature with 5.58 g (22 mmol) of iodine and stirred under nitrogen atmosphere for 24 hours at 60° C. Under reduced pressure, the acetic acid is largely distilled off and the residue is taken up in 100 ml of water. The water phase is extracted 3 times with 100 ml of ethyl acetate each. The ethyl acetate phases are washed with sodium thiosulfate solution and dried on sodium sulfate. After concentration by evaporation of the solution, 10 g of crude product is obtained. Recrystallization from ethyl acetate yields 8.8 g of 17β-acetoxy-2-iodo-1α-methyl-androst-4-en-3-one (93% of theory) of melting point 102° C.

Provenance & Evidence