Propargyl alcohol → HCID 19426838, compound

Participants

Reaction Steps

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.

Provenance & Evidence