Cholesterol → (3beta)-3-Hydroxycholest-5-en-7-one

Participants

Reaction Conditions

Reaction Steps

Cholesterol (13, 1.93 gm, 0.005 mol) and tert-butyl hydroperoxide (4.2 ml of 70% aq. solution, 0.03 mol) were dissolved in dichloromethane (20 ml). The mixture was stirred vigorously, cooled to 0-5° C. and a dilute solution of sodium hypochlorite (15 ml, 5.25% available chlorine) was added slowly in the form of fine, small droplets during ten hours at 0-5° C. After completion of addition, the dichloromethane layer was separated, washed with water, aqueous sodium bisulfite solution (10%, 2×10 ml) and water. The organic solvent was evaporated under reduced pressure to yield a crude product, which was chromatographed on a silica gel column utilizing 20% acetone in petroleum-ether to afford 1.35 gm (67.5%) of 7-oxo-cholesterol (14) as a snow white solid having a melting point of 169-70° C.

Provenance & Evidence