반응 #948750

반응 방정식

sodium cyclopentadienylide

→

colourless oil

수율 69.0%

3-butenylcyclopentadiene

수율 69.0%

용매

THF

THF

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   추출the product extracted with ether (3×75 ml)
3. 3
   건조The combined organic fractions were dried over magnesium sulphate for 2 hours
4. 4
   여과filtered
5. 5
   기타the solvents removed under reduced pressure
6. 6
   기타a rotary evaporator
7. 7
   기타to yield a dark brown oil
8. 8
   workup.DISTILLATIONThe crude product was distilled under reduced pressure (b.p. 50°-51° C. @15 mm Hg)

실험 절차

To a solution of 25.0 g (110 mmol) 3-buten-1-tosylate prepared according to step (a) above in 200 ml THF cooled to 0° C. was added 68.9 ml of 2.0M (138 mmol) sodium cyclopentadienylide in THF. The reaction mixture was allowed to warm to room temperature and was stirred for 16 h. 100 ml concentrated aqueous saline solution was added and the product extracted with ether (3×75 ml). The combined organic fractions were dried over magnesium sulphate for 2 hours, filtered and the solvents removed under reduced pressure using a rotary evaporator to yield a dark brown oil. The crude product was distilled under reduced pressure (b.p. 50°-51° C. @15 mm Hg) to give 5.71 g of a colourless oil (47.6 mmol, 43.3%).

출처