Triethylamine → Ethyl 3-(5-hydroxypyridin-2-yl)prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

The mixture of 6-bromopyridin-3-ol (5.22 g, 30.0 mmol), ethyl acrylate (4.51 g, 45.0 mmol), palladium acetate (175 mg, 0.78 mmol), tri-o-tolylphosphine (438 mg, 1.44 mmol), and triethylamine (4.55 g, 45.0 mmol) in N,N-dimethylformamide was placed in a sealed tube, and the mixture was stirred at 140° C. for 24 h. The mixture was quenched with water (100 mL), extracted with ethyl acetate (100 mL×3). The combined organic layer was washed with water (100 mL×4), brine (50 mL), dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:1) to give 2.3 g (40%) of the title compound as a yellow oil. ((E), (Z) mixture)

Provenance & Evidence