Hydrochloric Acid → HCID 19426814, compound

Participants

Reaction Steps

The acetylenic alcohol product of Example 33, Step 2 (14, 2.2 g, 7.4 mmol) was dissolved in ether (20 ml) and treated dropwise with a solution of 3.2 ml of sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al, 3.2 ml, 70% in toluene) in toluene (10 ml) under a nitrogen atmosphere. The reaction mixture was refluxed for 2 hours, allowed to cool to room temperature and then a solution of aqueous 1N HCl (50 ml) was carefully added. The mixture was filtered and insolubles washed with ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (30 ml×2). The combined organic phases were washed with aqueous NaHCO3 (100 ml) and brine (100 ml), then were dried (MgSO4) and solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:1) to afford 1.7 g (77% yield) of the title compound (19).

Provenance & Evidence