HCID 67924099, compound → HCID 67924091, compound

Participants

Reaction Steps

A solution of 3β-benzoyloxy-14α-carbethoxymethyl-5α-cholest-8,15-diene (2.06 g, 3.58 mmole) in THF (90 mL), absolute ethanol (40 mL) and 20% ethanolic sodium ethoxide (5 mL) was heated at 75° C. for one hour. The reaction was partitioned between ethyl ether and iced dilute HCl. The organic layer was washed with water, dried and concentrated to yield the crude 14α-carbethoxymethyl-5α-cholest-8,15-dien-3β-ol. This was dissolved in ethyl acetate (150 mL) and platinum oxide (1 g) was added. The mixture was agitated under an atmosphere of hydrogen for 2 hours. The catalyst was filtered and the concentrated filtrate was flash chromatographed with 2:1 to 1:1 hexane in ethyl acetate to yield 1.59 g of 14α-carbethyoxymethyl-5α-cholest-8-en-3β-ol; mp 72°-73° C. (from CH3CN).

Provenance & Evidence