Sodium Hydroxide → HCID 10311032, compound

Participants

Reaction Steps

Ex-4: {4-[3-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-propynoyl]-2,6-dimethoxy-phenoxy}-acetic acid methyl ester (500 mg, 1.01 mmol) from Ex-3 was dissolved in THF (5 mL) and methanol (5 mL). Sodium hydroxide solution (1 N, 5 mL) was added and the resulting solution was stirred at room termperature under nitrogen for 30 min. The reaction-was then diluted with 1 N HCl and isopropyl acetate and the layers cut. The organic phase was concentrated to dryness under reduced pressure, diluted with a small amount of ethanol and filtered to afford 350 mg (73%) of the desired {4-[3-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-propynoyl]-2,6-dimethoxy-phenoxy}-acetic acid as a yellow solid, m.p. 192–194° C. 1H-NMR (300 MHz, d6-DMSO) δ 7.95 (s, 1H), 7.56 (dd, 1H, J=3.5 and 1.4 Hz), 7.49 (m, 1H), 7.47 (s, 2H), 7.07 (dd, 1H, J=5.1 and 3.5 Hz), 6.86 (s, 1H), 4.61 (s, 2H), 4.00 (s, 3H), 3.97 (s, 3H), 3.84 (s, 6H).

Provenance & Evidence