Synthesis
To 12 mL of pyridine, 10.0 g of 3-furaldehyde and 15.0 g of malonic acid were added and heated with stirring at 80°C to 90°C for 2 hours. Upon completion of the reaction, the reaction solution was poured into ice water and the pH was adjusted to weakly acidic with 1 N hydrochloric acid. The precipitated crystals were collected by filtration, dissolved in ethyl acetate and the organic phase was washed with 1 N hydrochloric acid. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized by ethyl acetate-hexane mixed solvent to give 11.78 g (82% yield) of 3-(3-furyl)acrylic acid. The product was characterized by 1H-NMR (CDCl3): δ 7.70-7.67 (m, 2H), 7.45 (s, 1H), 6.62-6.61 (m, 1H), 6.16 (d, J = 15.8 Hz, 1H). Mass spectral analysis showed m/e: 138 (M+, base peak).
References
[1] Organic and Biomolecular Chemistry, 2010, vol. 8, # 24, p. 5483 - 5485
[2] ChemMedChem, 2018, vol. 13, # 18, p. 1972 - 1977
[3] Heterocycles, 1984, vol. 22, # 8, p. 1747 - 1757
[4] Patent: EP1724267, 2006, A1. Location in patent: Page/Page column 128
[5] Patent: WO2016/37578, 2016, A1. Location in patent: Page/Page column 111
