1,3-Dibromo-5,5-dimethylhydantoin → HCID 54401871, compound

Participants

Reaction Conditions

Reaction Steps

1α,2α,3β-Triacetoxy-cholesta-5-ene (300 mg) was dissolved in a mixture of petroleum benzine (5 ml) and benzene (5 ml). To the solution was added 1,3-dibromo-5,5-dimethyl hydantoin (95 mg) and the resulting solution was heated on water bath at 70° C for 20 minutes. After cooling the solution, precipitated crystals was filtrated off and the filtrate was concentrated under reduced pressure to dryness. The resulting bromide (3 ml) as crude product was dissolved in xylene. A mixture of trimethyl phosphite (1 ml) and xylene (3 ml) was added dropwise to the solution while refluxing it mildly in an argon stream. After continuously refluxing for 2 hours, the solvent was distilled off. The resulting 1α,2α,3β-triacetoxy-cholesta-5,7-diene was dissolved in diethyl ether (10 ml) and to the solution was added slowly 4-phenyl-1,2,4-triazoline-3,5-dione. About 25 mg of triazoline was required. After continuously stirring the mixture for 1 hour, diethyl ether was distilled off and then the residue was subjected to column chromatography with the use of alumina column and a solvent (diethyl ether : hexane = 1 : 1) to obtain 1,4-addition product of 1α,2α,3β-triacetoxy-cholesta-5,7-diene as oil represented by the formula ##STR6## wherein Ac is an acetyl.

Provenance & Evidence