Acetic Acid → HCID 13922882, compound

Participants

Reaction Conditions

Reaction Steps

The acetyl compound from Example 38 (1.79 g, 7 mmole) was dissolved in 40 ml of CH3OH, cooled to 0° C. and NaBH4 (264 mg, 7 mmole) in 4 ml of 40% NaOH was added. The reaction mixture was stirred for 25 minutes then 2.5 g of NH4Cl was added followed by 1 ml glacial acetic acid. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (75 ml) and 20% saturated NaHCO3 (50 ml). The ethyl acetate layer was washed with H2O (50 ml) and the combined aqueous solution was back-extracted with ethyl acetate. The ethyl acetate extracts were combined and dried over Na2SO4. The solvent was removed in vacuo and the residue was crystallized from CHCl3 -dichloroethane yielding 1.56 g (86.7%) of product, m.p. 134°-35° C.

Provenance & Evidence