反应 #9894

反应方程式

NBS

undec-10-en-1-ol

triphenylphosphine

→

11-bromo-undec-1-ene

收率 82.3%

溶剂

DMF

反应条件

后处理

1. 1
   其他the reaction was quenched with methanol (0.5 mL)
2. 2
   workup.ADDITIONThe solution was diluted with ether (80 mL)
3. 3
   洗涤washed with water, saturated aqueous NaHCO3 and brine successively
4. 4
   其他The organic layer was dried
5. 5
   浓缩concentrated
6. 6
   其他The residue was purified by flash chromatography on silica gel
7. 7
   洗涤eluting with hexane

实验过程

To a solution of undec-10-en-1-ol (0.86 g, 5.0 mmol) in DMF (15 mL) was added triphenylphosphine (1.46 g, 5.6 mmol). The solution was cooled to 0° C. and NBS (0.96 g, 5.4 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.5 mL). The solution was diluted with ether (80 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford 11-bromo-undec-1-ene (0.96 g, 82%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.79 (1H, m), 4.93 (2H, m), 3.38 (2H, t, J=6.9 Hz), 2.02 (2H, m), 1.83 (2H, m), 1.20–1.55 (12H, m); 13C NMR (75 MHz, CDCl3) δ 139.36, 114.33, 34.27, 33.99, 33.01, 29.57×2, 29.27, 29.09, 28.94, 28.35.

来源