반응 #95467

반응 방정식

phosphorous tribromide

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

→

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

용매

ether

ether

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도under reflux for 2.5 h
3. 3
   workup.ADDITIONpoured onto ice-water
4. 4
   추출It was extracted three times with ether
5. 5
   세척The combined ether extracts were washed with dilute aqueous sodium bicarbonate solution, water
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated in vacuo
8. 8
   workup.DISTILLATIONEvaporative distillation of the crude product at 145°-148° C./0.15 mm

실험 절차

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.

출처