Methyl Acrylate → 3-Pyridin-4-YL-acrylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromopyridine (40.6 g, 0.25 mmol), palladium acetate (1.16 g, 5.14 mmol), tri-(O-tolyl)phosphine (3.14 g, 10.3 mmol), CH3CN (129 mL), triethylamine (64.3 mL, 0.46 mmol) and methyl acrylate (46.8 mL, 0,514 mmol) was sealed in a bomb and placed in an oil bath at 120° C. for 4 hours. The mixture was cooled to 0° C., the bomb was vented, and the slurry thus obtained was partitioned between CH2Cl2 /water. The aqueous phase was separated, extracted with CH2Cl2 (2×200 mL) and the combined organic layers were dried over MgSO4. The solvent was removed in vacuo to afford 38 g of methyl 3-(4-pyridyl)propenoate.

Provenance & Evidence