Реакция #948477

Уравнение реакции

sodium cyclopentadienylide

→

3-butenylcyclopentadiene

Выход 69.0%

colourless oil

Выход 69.0%

Растворители

THF

THF

Условия реакции

Обработка

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

Методика

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%).

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