反应 #95467

反应方程式

phosphorous tribromide

(Z,Z)-5,8-tetradecadien-2-yn-1-ol

→

(Z,Z)-1-bromo-5,8-tetradecadien-2-yne

溶剂

ether

ether

反应条件

后处理

1. 1
   温度The reaction mixture was heated
2. 2
   温度under reflux for 2.5 h
3. 3
   workup.ADDITIONpoured onto ice-water
4. 4
   萃取It was extracted three times with ether
5. 5
   洗涤The combined ether extracts were washed with dilute aqueous sodium bicarbonate solution, water
6. 6
   干燥dried over Na2SO4
7. 7
   浓缩concentrated in vacuo
8. 8
   workup.DISTILLATIONEvaporative distillation of the crude product at 145°-148° C./0.15 mm

实验过程

A solution of phosphorous tribromide (0.47 g, 1.73 mmol) in absolute ether (0.5 ml) was added dropwise during five minutes to a mixture of (Z,Z)-5,8-tetradecadien-2-yn-1-ol (1.03 g, 5 mmol), and dry pyridine (14 mg, 0.18 mmol) in 8 ml of absolute ether. The reaction mixture was heated under reflux for 2.5 h, cooled to 23° C., then poured onto ice-water. It was extracted three times with ether. The combined ether extracts were washed with dilute aqueous sodium bicarbonate solution, water, dried over Na2SO4 and concentrated in vacuo. Evaporative distillation of the crude product at 145°-148° C./0.15 mm afforded 1.1 g (80.5%) of (Z,Z)-1-bromo-5,8-tetradecadien-2-yne as a pale yellow oil.

来源