4-Pyridinecarboxaldehyde → HCID 10352231, compound

Participants

Reaction Steps

A solution of 4-pyridinecarboxaldehyde (333 mg, 3.11 mmol) and (carboethoxy-methylene)triphenylphosphorane (1.19 g, 3.42 mmol) in toluene (8.0 ml) was stirred at 90° C. under nitrogen for 3 hours. Once cooled, the solvent was removed under reduced pressure, the crude product was acidified with 1M HCl (25 ml) and the solution was washed with Et2O (25 ml×2). The aqueous solution was made basic with 1M NaOH and extracted with CH2Cl2 (25 ml×2). The combined organic solution was dried (Na2SO4), filtered and concentrated under reduced pressure, giving (E)-3-pyridin-4-yl-acrylic acid ethyl ester as a white solid (238 mg, 1.34 mmol, 43%). 1H NMR (CDCl3) δ 1.35 (t, 3H, J=7.2 Hz), 4.29 (q, 2H, J=7.2 Hz), 6.59 (d, 1H, J=16.2 Hz), 7.37 (d, 2H, J=6.1 Hz), 7.60 (d, 1H, J=16.2 Hz), 8.66 (d, 2H, J=6.1 Hz).

Provenance & Evidence