HCID 15124020, compound → HCID 15124021, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methyl-4-hydroxy-5-tert-butyl-7-(2-thienoyl)-benzofuran-2-carboxylic acid (0.345 g, 0.96 mmol) in quinoline (1.0 mL) at room temperature was added fine copper powder (0.061 g, 0.96 mmol). The reaction mixture was flushed with nitrogen and heated in an oil bath to 200° C. until all CO2 evolution had ceased (about 20 min.). The reaction mixture was cooled to room temperature and poured into 30 mL 2N HCl. The aqueous solution was extrated with EtOAc (3×15 mL). The combined organic extracts were washed with 2N HCl (2×10 mL), water (10 mL) and saturated NaCl (10 mL) and dried over Na2SO4. Filtration, concentration and flash chromatography (85:15, hexane:EtOAc) afforded pure compound 14. 1H NMR d 1.5 (9H, s), 2.5 (3H, s), 5.74 (1H, s), 7.18 (1H, dd, J=4 Hz), 7.34 (1H, s), 7.68 (1H, d, J=4 Hz), 7.73 (1H, d, J=4 Hz), 7.74 (1H, s).

Provenance & Evidence