Propargyl alcohol → HCID 19426838, compound

To a solution of the product of Step 1, above (13, 5.5 g, 15 mmol) in triethylamine (40 ml), was added bis(triphenylphosphine)palladium (II) chloride (0.63 g, 0.9 mmol) and propargyl alcohol (1.4 g, 25 mmol) under a nitrogen atmosphere. After stirring at room temperature for 1 hour, Cul (0.25 g, 1.3 mmol) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 18 hours, insolubles were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (100 ml) and water (100 ml) and the aqueous layer were separated and extracted with ethyl acetate (100 ml×2). The combined organic layers were washed with aqueous 1N HCl (150 ml), aqueous NaHCO3 (150 ml) and brine (150 ml), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:4) to give 4.3 g (95% yield) of the title compound (14) as pale yellow solids.

1. additionCul (0.25 g, 1.3 mmol) was added to the reaction mixture
2. stirringThe reaction mixture was stirred at room temperature for 18 hours
3. custominsolubles were removed by filtration
4. concentrationthe filtrate was concentrated under reduced pressure
5. customThe residue was partitioned between ethyl acetate (100 ml) and water (100 ml)
6. customthe aqueous layer were separated
7. extractionextracted with ethyl acetate (100 ml×2)
8. washThe combined organic layers were washed with aqueous 1N HCl (150 ml), aqueous NaHCO3 (150 ml) and brine (150 ml)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:4)

ORD record

ord-656820a9334148cdb1236bebed12b52d

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05552424