Methanol → HCID 15124001, compound

Participants

Reaction Steps

To a solution of potassium hydroxide (1.96 g, 34.86 mmol) in water (75 mL) was added compound 1 (4.00 g, 11.62 mmol) and the resulting suspension was heated to reflux for two hours. During the reflux a small portion of methanol was rinsed into the reaction mixture. After cooling, the reaction mixture was diluted with water (225 mL) and acidified with 2N HCl (25 mL). The resulting suspension was cooled in an ice bath, and the product collected by filtration. After vacuum drying, 3-methyl-4-methoxy-7-(2-thienoyl)-benzofuran-2-carboxylic acid, compound 2, was obtained. mp 252°-255° C.; 1H NMR d 2.80 (3H, s), 2.80 (1H, br s), 4.06 (3H, s), 6.76 (1H, d, J=8 Hz), 7.19 (1H, m), 7.70 (1H, dd, J=4 Hz, 1 Hz), 7.76 (1H, dd, J=4 Hz, 1 Hz), 7.90 (1H, d, J=8 Hz).

Provenance & Evidence