Hydrochloric Acid → HCID 19426814, compound

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).

1. temperatureThe reaction mixture was refluxed for 2 hours
2. filtrationThe mixture was filtered
3. washinsolubles washed with ethyl acetate and water
4. extractionThe aqueous phase was extracted with ethyl acetate (30 ml×2)
5. washThe combined organic phases were washed with aqueous NaHCO3 (100 ml) and brine (100 ml)
6. dry with materialwere dried (MgSO4) and solvent
7. customwas removed under reduced pressure
8. customThe residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:1)

ORD record

ord-f87b5a5c4f6e4d7e83faee7c04569c65

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05552424