反应 #9908

反应方程式

NBS

6-cyclohexyl-hexan-1-ol

triphenylphosphine

→

(6-bromo-hexyl)-cyclohexane

收率 89.0%

溶剂

DMF

反应条件

后处理

1. 1
   其他the reaction was quenched with methanol (0.6 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 6-cyclohexyl-hexan-1-ol (0.98 g, 5.3 mmol) in DMF (15 mL) was added triphenylphosphine (1.56 g, 5.9 mmol). The solution was cooled to 0° C. and NBS (1.02 g, 5.7 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.6 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 (6-bromo-hexyl)-cyclohexane (1.16 g, 89%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.41 (2H, t, J=7.2 Hz), 1.85 (2H, m), 1.66 (5H, m), 1.42 (2H, m), 1.08–1.36 (10H, m), 0.88 (2H, m); 13C NMR (75 MHz, CDCl3) δ 37.91, 37.68, 34.37, 33.72, 33.14, 29.39, 28.51, 27.04, 26.96, 26.73.

来源