反应详情

To ethyl 4-(2-bromophenyloxy)but-2-enoate (6.10 g, 21.0 mmol) in benzene (200 mL) at reflux was added AIBN (0.07 g, 0.4 mmol) followed by dropwise addition of a benzene (~65 mL) solution containing tri-n-butyltin hydride (6.72 g, 23.1 mmol). After complete addition (one h) the reaction was refluxed an additional 2 h. The reaction was concentrated in vacuo and the residue treated with Et2O (~50 mL) and a 60% KF solution (~40 mL). The solution was stirred 14 h. The precipitate was removed by filtration and the Et2O phase decanted off. The remaining aqueous phase was extracted with Et2O (3×). The combined Et2O solutions were washed with saturated aqueous NaCl solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (95:5 Hexane:EtOAc) afforded the title compound (4.12 g, 88%).

1. additionAfter complete addition (one h) the reaction
2. temperaturewas refluxed an additional 2 h
3. concentrationThe reaction was concentrated in vacuo
4. additionthe residue treated with Et2O (~50 mL)
5. customThe precipitate was removed by filtration
6. customthe Et2O phase decanted off
7. extractionThe remaining aqueous phase was extracted with Et2O (3×)
8. washThe combined Et2O solutions were washed with saturated aqueous NaCl solution
9. dry with materialdried with anhydrous MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo