Acetic Acid → HCID 53961427, compound

Participants

Reaction Conditions

Reaction Steps

Calcium chloride (15.0 g) was dissolved in methanol (150 ml) and cooled to -10° C . To a cooled solution was added dropwise while keeping at -10° C. a solution of sodium borohydride (7.5 g) in ethyl alcohol (150 ml) and the solution was stirred at the same temperature for 30 minutes. A solution of ergosta-1,3,5,7,22-pentaen-3-ylacetate (III) (5.0 g) from Example 1 in diethyl ether (100 ml) was added dropwise at a temperature between -5° and -10° C. The reaction mixture was stirred at a temperature between 0° and -5° C. for 3 hrs. and then at room temperature for 3 hrs. 50% Acetic acid was added to prepare a uniform solution and the solution was extracted with ethyl acetate. The extract was washed with water, then an aqueous sodium bicarbonate solution and dried. Ethyl acetate was concentrated and the residue was purified by silica gel chromatography (eluted with chloroform) followed by crystallization with acetone to give 4.2 g (90% yield) of ergosta-1,5,7,22-tetraen-3β-ol (I), m.p. 156°-157° C.

Provenance & Evidence