Hydrochloric Acid → HCID 15124022, compound

Participants

Reaction Steps

To a solution of ethyl 3-methyl-4-hydroxy-5-tert-butylbenzofuran-2-carboxylate, compound 12a (1.00 g, 3.62 mmol) and benzoyl chloride (0.763 g, 5.43 mmol) in 1,2-dichloroethane (40 mL) at 0° C. was added aluminum chloride (0.720 g, 5.43 mmol) and the resulting mixture warmed to reflux for 3.5 hours. The reaction was allowed to cool, poured into 2N HCl (100 mL) and extracted with methylene chloride (4×25 mL). The combined extracts were washed with 5% NaHCO3 (25 mL), dried (Na2SO4), and concentrated. Flash chromatography using 25% ethyl acetate in hexane as eluant afforded ethyl 3-methyl-4-hydroxy-5-tert-butyl-7-benzoylbenzofuran-2-carboxylate, compound 15 as an oil sufficiently pure for further chemistry. 1H NMR d 1.34 (3H, t, J=6 Hz), 1.51 (9H, s), 2.89 (3H, s), 4.35 (2H, q, J=6 Hz), 7.56 (3H, m), 7.86 (3H, m).

Provenance & Evidence