Acetic Acid → HCID 86745125, compound

Participants

Reaction Steps

The silyl ether from Step C (230 mg, 0.00024 mol) was dissolved in 5 ml of tetrahydrofuran (THF) and treated with 54 μl, (0.057 g, 0.00095 mol) of acetic acid and 710 μl (1M in THF, 0.00071 mol) of tetrabutylammonium fluoride (Bu4N F) and the mixture was stirred overnight at room temperature. Another 57 μl of acetic acid and 710 μl of Bu4N F were added and stirring was continued an additional 24 hours. The mixture was poured into 100 ml of ether and washed with 1×5 ml of 1N hydrochloric acid, 1×10 ml of saturated aqueous sodium bicarbonate and 2×10 ml of brine and dried (MgS04) Concentration to dryness gave 120 mg of an oil. The oil was chromatographed on a "Still" column of silica gel (1.5×17.7 cm, 230-400 mesh) by elution with 5% acetone in methylene chloride (v/v) collecting 5 ml fractions. Fractions 12-20 containing the product were combined and concentrated to dryness to give 53 mg of solid (m.p. 64°-66° C.). Recrystallization of a sample from hexane gave material with m.p. 67°-68° C.

Provenance & Evidence