反应详情

To a solution of methanesulfonic acid 4-(6-iodo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester (1.00 g, 1.89 mmol) in tetrahydrofuran (5 mL) was added a 2.5 N aqueous solution of sodium hydroxide (6.0 mL) and the biphasic reaction mixture was heated at reflux for 5 hours and then heated in a sealed pressure tube at 110 C. for about 18 hours. The reaction mixture was diluted with water (100 mL), acidified with 10% hydrochloric acid and the organics were extracted with ether (2×100 mL). The extracts were combined, washed with water (100 mL), concentrated and chased with petroleum ether to give the title compound (0.869 g, over theoretical); NMR (DMSO-d6); δ 9.85 (s, 1H, OH), 8.15 (d, J=8 Hz, 1H), 8.02 (d, J=8 Hz, 1H), 7.73 (ddd, J=8, 7, 1 Hz, 1H), 7.69-7.44 (m, 3H), 7.21-7.16 (m, 3H), 7.09-7.06 (m, 2H), 6.68 (d, J=8Hz, 1H).

1. customthe biphasic reaction mixture
2. temperaturewas heated
3. temperatureat reflux for 5 hours
4. temperatureheated in a sealed pressure tube at 110 C
5. extractionthe organics were extracted with ether (2×100 mL)
6. washwashed with water (100 mL)
7. concentrationconcentrated and chased with petroleum ether