HCID 57815270, compound → HCID 57815493, compound

Participants

Reaction Steps

To a solution of 16 g of 4-oxo-6-((tetrahydro-2H-pyran-2-yloxy)methyl)-4H-pyran-3-yl trifluoromethanesulfonate in 100 mL of acetonitrile, 5.1 mL of propargyl alcohol, 18 mL of triethylamine, 0.62 g of dichlorobis(triphenylphosphine)palladium(II) and 0.42 g of copper (I) iodide were added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 2 hours. The insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=100:0 to 97:3 to obtain 6.2 g of 5-(3-hydroxy-1-propyn-1-yl)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)-4H-pyran-4-one as a brown oily substance.

Provenance & Evidence