Hydrochloric Acid → HCID 15124024, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-4-hydroxy-5-t-butyl-7-benzoylbenzofuran-2-carboxylic acid (0.334 g, 0.98 mmol), quinoline (1 mL), and copper powder (0.062 g, 0.98 mmol) was warmed to 195° C. until gas evolution had ceased (about 10 minutes). The reaction mixture was allowed to cool and poured into 2N HCl (40 mL). Ethyl acetate (25 mL) was added and the biphasic mixture was filtered through a pad of celite. The layers were separated and the aqueous layer extracted with ethyl acetate (25 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Flash chromatography using 10% ethyl acetate in hexane as eluant afforded 3-methyl-4-hydroxy-5-tert-butyl-7-benzoylbenzofuran, compound 16 as a white solid after trituration from hexane. 1H NMR d 1.49 (9H, s), 2.51 (3H, d, J=2 Hz), 5.78 (1H, s), 7.31 (1H, s), 7.54 (3H, m), 7.66 (1H, s), 7.85 (2H, m).

Provenance & Evidence