反应详情

温度

68 °C

To a 25 ml round bottom flask was added 7-(4-hydroxyphenyl)-benzofuran-5-carbaldehyde (400 mg, 1.68 mmol), hydroxylamine hydrochlorode (234 mg, 3.36 mmol), anhydrous MeOH (10.4 ml), and anhydrous pyridine (0.272 ml, 3.36 mmol). The reaction was then heated to 68° C. and the reaction was brought to reflux for 1 h. The reaction was then 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 410 mg (96%) product as a yellow solid. The crude material was pure by 1H NMR (−4% cis isomer was detected) and LC-MS (one peak): mp 192–194° C. 1H NMR (300 MHz, DMSO-d6): δ 6.92 (2H, d, J=8.6 Hz), 7.05 (1H, d, J=2.2 Hz), 7.69–7.72 (3H, m), 7.79 (1H, d, J=1.4 Hz), 8.09 (1H, d, J=1.1 Hz), 8.27 (1H, s), 9.74 (1H, s), 11.14 (1H, s); MS (ESI) m/z 254 ([M+H]+).

1. temperatureto reflux for 1 h
2. temperatureThe reaction was then cooled to room temperature
3. customthe layers separated
4. washThe ether layer was washed with water
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated to 410 mg (96%) product as a yellow solid