Cholesterol → HCID 53755109, compound

Participants

Reaction Steps

Cholesterol derivative 12 (1 mmole) in 40 ml of CCl4 is treated with 600 mg NaHCO3 and 170 mg of 1,3-dibromo-5,5-dimethyl hydantoin, and the mixture is refluxed under N2 for 3 hours. After cooling to 0° C. the solid hydantoin is removed by filtration. The filtrate is evaporated, the residue is redissolved in 5 ml xylene at 140° C. After 1.5 hours under N2 at this temperature the mixture is cooled to room temperature, diluted with benzene, and washed with 5% HCl, 4% NaHCO3 and saturated NaCl solution. After drying (using Na2SO4) the solvent is evaporated and the residue is chromatographed on AgNO3 -impregnated thin layer plates developed with ethyl acetate/Skellysolve B (1:4). This yields pure 5,7-diene (13) of molecular weight 440 and exhibiting the typical 5,7-diene ultraviolet spectrum.

Provenance & Evidence