反应详情

A mixture of 4-benzyloxy-7-hydroxycoumarin (5.36; 0.02 mole) anhydrous potassium carbonate (4.0 g) and 1-bromo-2-(4-fluorophenyl) ethane (4.06 g) in acetone (100 ml) was stirred at reflux for 20 hours and the inorganic material filtered off. Evaporation of the filtrate in vacuo gave an oil which rapidly set solid on scratching. Chloroform (200 ml) was added and the mixture filtered to remove unchanged 4-benzyloxy-7-hydroxycoumarin. Reevaporation of the filtrate afforded a white solid, 3.34 g (43%) of m.p. 120°, νmax (mull) 1715, 1675, 1620 cm-1 ; τ(CDCl3); 6.93 (2H, t, J 6.7 Hz); 5.80 (2H, t, J 6.7 Hz); 4.87 (2H,S); 4.38 (1H,); 3.29-2.49 (6H, m) 2.32 (1H, d, J 10 Hz); (Found C, 73.75 H, 5.14 C24H19FO4 requires; C, 73.84; H, 4.91%).

1. temperatureat reflux for 20 hours
2. filtrationthe inorganic material filtered off
3. customEvaporation of the filtrate in vacuo
4. customgave an oil which rapidly set solid
5. filtrationthe mixture filtered
6. customto remove unchanged 4-benzyloxy-7-hydroxycoumarin
7. customReevaporation of the filtrate
8. customafforded a white solid, 3.34 g (43%) of m.p. 120°, νmax (mull) 1715, 1675, 1620 cm-1