Triethylamine → HCID 22991227, compound

Participants

Reaction Conditions

Reaction Steps

In a flask equipped with a stirrer and a thermometer, 13.36 g of 1-iodo-4-perhydro-2H-pyrane-2-yloxy-3-methylbenzene prepared in Step 2-1, 0.24 g of dichlorobis(triphenylphosphine)palladium, 0.24 g of triphenylphosphine, 0.12 g of copper iodide (I), and 12.75 g of triethyl amine were suspended in 50 g of ethylacetate under a nitrogen atmosphere, and heated up to 58° C. under stirring. Then a solution of 6.20 g of trimethylsilylacetylene and 6.20 g of ethylacetate was added dropwise at 58 to 64° C. over 2 hours. The resulting mixture was stirred at the same temperature for 3 hours, cooled down to room temperature, and filtered. The residue was washed with ethylacetate, and the resulting filtrate was concentrated at 60° C. under a pressure of 20 Torr. The concentrate was purified through silica gel chromatography using hexane mixed with 0.1 wt % triethyl amine as an eluting solvent, to thereby obtain 11.87 g of 2-(4-(trimethylsilylethynyl)-2-methylphenoxy)perhydro-2H-pyrane at 98% yield.

Provenance & Evidence