Triethylamine → (E)-tert-butyl 3-(6-methylpyridin-3-yl)acrylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-methylpyridine (5 g, 29.06 mmol) in NMP (60 mL), were added Pd(OAc)2 (0.325 g, 1.45 mmol) and P(o-tol)3 (0.883 g, 2.9 mmol). Subsequently, a solution of tert-butyl acrylate (13.02 g, 101.7 mmol) in Et3N (16.1 mL, 116.2 mmol) was added under N2 to the above mixture and stirred at 90° C. After 16 h, water was added to the reaction mixture and extracted with Et2O (3×). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo to afford a residue. Purification of the residue by column chromatography (SiO2, 100-200 mesh, Et2O/Pet ether 1:9) afforded the title compound. MS: 220 [M+H]+;

Provenance & Evidence