反応 #948750

反応方程式

sodium cyclopentadienylide

→

colourless oil

収率 69.0%

3-butenylcyclopentadiene

収率 69.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   温度to warm to room temperature
2. 2
   抽出the product extracted with ether (3×75 ml)
3. 3
   乾燥The combined organic fractions were dried over magnesium sulphate for 2 hours
4. 4
   ろ過filtered
5. 5
   その他the solvents removed under reduced pressure
6. 6
   その他a rotary evaporator
7. 7
   その他to yield a dark brown oil
8. 8
   workup.DISTILLATIONThe crude product was distilled under reduced pressure (b.p. 50°-51° C. @15 mm Hg)

実験手順

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%).

出典