反应详情

温度

-78 °C

To a solution of ethyl trans-4-bromocinnamate (8 mL, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added diisobutylaluminum hydride in dichloromethane (128 mL, 1 M, 128 mmol) at −78° C. dropwise. After the addition, the mixture was allowed to warm from −78° C. to −30° C. over two hours. The mixture was then cooled back to −78° C. and aqueous 1 N HCl was added till acidic (pH=2). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried with MgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 1.44 (t, J=6 Hz, 1H), 4.32 (t, J=4.5 Hz, 2H), 6.37 (dt, J=16.5 Hz, J=6 Hz, 1H), 6.57 (dt, J=15 Hz, J=3 Hz, 1H), 7.25 (d, J=9 Hz, 2H), 7.45 (d, J=9 Hz, 2H). MS (DCl—NH3) m/z 214 (M+H)+.

1. additionAfter the addition
2. temperatureto warm from −78° C. to −30° C. over two hours
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with dichloromethane
5. dry with materialThe combined organic layers were dried with MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure