反应 #1152261

反应方程式

triphenylphosphine

bicyclo[2.2.1]hept-5-ene-2-methanol

carbon tetrachloride

→

5-chloromethylbicyclo[2.2.1]hept-2-ene

反应条件

后处理

1. 1
   温度heated at 60° for 6 h
2. 2
   温度After cooling
3. 3
   过滤the reaction mixture was filtered
4. 4
   其他the filtrate was evaporated under reduced pressure
5. 5
   其他to afford a semi-crystalline mass, which
6. 6
   其他was triturated with n-pentane (100 ml)
7. 7
   过滤The reaction mixture was filtered
8. 8
   浓缩the filtrate was concentrated under reduced pressure
9. 9
   其他to afford a yellow oil
10. 10
    workup.DISTILLATIONDistillation of the oil

实验过程

A mixture of triphenylphosphine (20.98 g, 0.08 mol) and bicyclo[2.2.1]hept-5-ene-2-methanol (5.0 g, 0.0403 mol) in dry carbon tetrachloride (31.5 ml) was stirred and heated at 60° for 6 h. After cooling, the reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to afford a semi-crystalline mass, which was triturated with n-pentane (100 ml). The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to afford a yellow oil. Distillation of the oil afforded 5-chloromethylbicyclo[2.2.1]hept-2-ene as a colourless oil, b.p. 70°-72°/24 mm Hg.

来源