Triethylamine → HCID 58047434, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-ethoxypyridine (5.00 g, 24.8 mmol) in THF (50 mL)-triethylamine (25 mL) were added trimethylsilylacetylene (5.3 mL, 37.2 mmol), copper(I) iodide (237 mg, 1.24 mmol) and bis(triphenylphosphine)palladium(II) chloride (870 mg, 1.24 mmol), and the mixture was stirred under an argon stream at 60° C. for 1 hr. Water was added to the reaction mixture, the mixture was extracted twice with hexane, and the combined organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=19:1) to give an oil. To a solution of the oil in THF (50 mL) was added 1 M tetrabutylammonium fluoride THF solution (26.0 mL, 26.0 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted twice with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=19:1) to give the title compound (690 mg, yield 19%) as an oil.

Provenance & Evidence