反応 #95467

反応方程式

phosphorous tribromide

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

→

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

溶媒

ether

ether

反応条件

後処理

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
   抽出It was extracted three times with ether
5. 5
   洗浄The combined ether extracts were washed with dilute aqueous sodium bicarbonate solution, water
6. 6
   乾燥dried over Na2SO4
7. 7
   濃縮concentrated in vacuo
8. 8
   workup.DISTILLATIONEvaporative distillation of the crude product at 145°-148° C./0.15 mm

実験手順

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.

出典