Acetic Acid → HCID 13491249, compound

Participants

Reaction Steps

Zinc chloride (5 g., 0.03 mole) was dissolved in 60 mL of diethyl ether and the insoluble material was filtered. The ethereal solution was added dropwise to sodium borohydride (3.5 g., 0.009 mole) in 150 mL of ether. The reaction mixture was stirred overnight at room temperature. The separated solid was allowed to settle and the supernatent liquid was removed by decantation. This ethereal solution of zinc borohydride was added to a solution of 4 g. (0.01 mole) of 13-acetylamino-6,7,8,9,10,11-hexahydro-3-acetyloxy-5-methyl-5,11-methanobenzocyclodecen-12(5H)-one in 50 mL of diethyl ether and the reaction mixture was stirred at room temperature for 48 hours. Excess zinc borohydride was decomposed by adding 3 mL of glacial acetic acid in 15 mL of water. The reaction mixture was filtered and the layer was washed with water, dried (anhydrous Na2SO4) and evaporated under reduced pressure. The separated solid was slurred in methanol and was heated while adding a few drops of dilute hydrochloric acid. The solvent was evaporated under vacuo and the solid was chromatographed on silica gel using ethyl acetate as eluent which afforded 2.3 g. (80.9% yield) of the title compound, mp 246°-249° C.

Provenance & Evidence