Methanol → HCID 136334157, compound

Participants

Reaction Conditions

Reaction Steps

To a 15 ml round bottom flask was added 7-(4-hydroxyphenyl)-benzofuran-4-carbaldehyde (250 mg, 1.05 mmol), hydroxylamine hydrochloride (146 mg, 2.10 mmol), anhydrous MeOH (6.5 ml), and anhydrous pyridine (0.17 ml, 2.10 mmol). The flask was then sealed and heated to 68° C. for 1 h, cooled to room temperature, dilute with ether, and the layers separated. The ether layer was washed with water, dried over anhydrous Na2SO4, passed through a silica plug, and concentrated to 250 mg (94%) clean product as a yellow solid. Further purification was done by chromatography (1:1 EtOAc/hexanes) for analytical analysis: mp 216–217° C.; 1H NMR (300 MHz, DMSO-d6): δ 6.92 (2H, d, J=8.7 Hz), 7.36 (1H, d, J=2.1 Hz), 7.49 (2H, app s), 7.74 (2H, d, J=8.6 Hz), 8.14 (1H, d, J=2.1 Hz), 8.42 (1H, s), 9.73 (1H, s) 11.36 (1H, s); MS (ESI) m/z 254 ([M+H]+).

Provenance & Evidence