Acetic Acid → HCID 57014607, compound

Participants

Reaction Steps

A solution of 10 (20.0 g, 30 mmole) in a mixture of 95% EtOH (200 mL) and CHCl3 (100 mL) was cooled in an ice bath and NaBH4 (3.4 g, 90 mmole) added portionwise over 10 min. The mixture was stirred for 90 min. in the cold, excess HOAc added to destroy the hydride and the solution evaporated. The residue was partitioned between CHCl3 and dilute NH4OH and further processed in the usual fashion. Evaporation gave a quantitative yield of 11 as a foam which contained traces of 6β-ol 2 and other impurities; NMR δ 4.41 (d, 1H, H5, J=5.5 Hz). This material was converted to 12 without further purification.

Provenance & Evidence