Formaldehyde → HCID 54145314, compound

Participants

Reaction Steps

A mixture of 19-hydroxy-4-androstene-3,17-dione, thiophenol, 40% aqueous formaldehyde, triethylamine and ethanol are heated at the reflux temperature for about 48 hours. The cooled solution is poured into an aqueous sodium hydroxide solution and the product isolated by ether extraction. The ether extract is washed with water, dried over magnesium sulfate and the solvent removed under reduced pressure. The residue is triturated with hot hexane to remove the condensation products derived from the thiophenol and formaldehyde. The 19-hydroxy-4-phenylthiomethyl-4-androsten-3,17-dione so obtained is desulfurized by dissolving in acetone and adding to a suspension of Raney Nickel in refluxing acetone. The mixture is heated at its reflux temperature while stirring for about 5 hours. The hot solution is filtered and the nickel washed with boiling ethanol and water. The combined filtrates are concentrated under vacuum whereupon the product separates as a solid. Recrystallization from an acetone-hexane solution yields 19-hydroxy-4-methyl-4-androstene-3,17-dione.

Provenance & Evidence