Triethylamine → 3-[(6-Methylpyridin-2-yl)ethynyl]cyclohex-2-en-1-one

Participants

Reaction Steps

A solution of 2-ethynyl-6-methyl-pyridine (702 mg, 6 mmol), 3-bromo-cyclohex-2-enone (1.26 g, 7.2 mmol), bis-(triphenylphosphine)palladium-dichloride (168 mg, 0.24 mmol), copper(I) iodide (93 mg, 0.48 mmol), triethylamine (4.8 ml, 34.4 mmol) in 12 ml DMF is heated to 55° C. for 1 h. After that time the solution is diluted with ethyl acetate (500 ml) and washed with sat aq. NaHCO3 (1×150 ml). The water phase is extracted with ethyl acetate (1×150 ml) and the combined organic phases are dried over Na2SO4, filtered and concentrated in vacuo. The residue (1.88 g) is purified on column chromatography (silica gel, eluent hexane/ethyl acetate 3:1 v/v) and the fractions containing the desired compound are collected and concentrated in vacuo to yield 1.05 g (yield=82%) of the title compound as a light yellow oil.

Provenance & Evidence