Pyridinium chloride → 7-(4-Hydroxyphenyl)-benzofuran-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a 10 ml round bottom flask was added 7-(4-methoxyphenyl)-benzofuran-5-carbaldehyde (0.50 g, 1.98 mmol), and pyridine hydrochloride (1.2 g, 5.2 mmol). The mixture was heated to 190° C. for 2 h, cooled slightly, then water (10 ml) was added to dissolve the remaining pyridine hydrochloride. The aqueous was extracted with EtOAc (3×), passed through a silica plug, and concentrated to 450 mg (96%) of crude product as a light yellow foam. The crude from this reaction was combined with a second batch (1 g scale reaction) and purified by column chromatography (1:1 EtOAc/Hexanes) to afford 760 mg of product as a yellow solid: mp 154–155° C.; 1H NMR (300 MHz, DMSO-d6): δ 6.95 (2H, d, J=8.6 Hz), 7.21 (1H, d, J=2.2 Hz), 7.76 (2H, d, J=8.6 Hz), 7.98 (1H, d, J=1.5 Hz), 8.19 (1H, d, J=1.5 Hz), 8.22 (1H, d, J=2.2 Hz), 9.81 (1H, s), 10.12 (1H, s); MS (ESI) m/z 237 ([M−H]−).

Provenance & Evidence