Chemical Properties
White solid
Uses
This compound is the starting material in the synthesis of (dihydro)benzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents.
Synthesis
a) Synthesis of (R,S)-2,3-dihydro-benzofuran-2-carboxylic acid (54a): commercially available benzofuran-2-carboxylic acid (Aldrich Chemical Company, 27 g, 167.7 mmol) was dissolved in ethyl acetate (300 mL). The hydrogenation reaction was catalyzed by 10% Pd/C (20 g) at 65-70 psi hydrogen pressure for 2 days. Upon completion of the reaction, the catalyst was removed by filtration and the solvent was evaporated. A solvent mixture of ethyl acetate-hexane (1:6) was added to the residue for recrystallization. Filtration afforded benzodihydrofuran-2-carboxylic acid as a crystalline solid (20.23 g, 74% yield). Melting point: 116-117 °C. 1H NMR (300 MHz, CDCl3) δ: 11.05 (brs, 1H), 7.17 (m, 2H), 6.91 (m, 2H), 5.24 (dd, 1H), 3.63 (dd, 1H), 3.42 (dd, 1H).
References
[1] Patent: US2005/54630, 2005, A1. Location in patent: Page/Page column 42
[2] Justus Liebigs Annalen der Chemie, 1883, vol. 216, p. 169
[3] Chemische Berichte, 1906, vol. 39, p. 496
[4] Farmaco, 1998, vol. 53, # 12, p. 764 - 772
[5] Patent: US2008/200540, 2008, A1. Location in patent: Page/Page column 18
