Реакция #1051366

Уравнение реакции

tetrahydrofurfuryltosylate

sodium cyclopentadienylide

→

colourless oil

Выход 46.9%

Tetrahydrofurfurylcyclopentadiene

Выход 46.9%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Температураto warm to room temperature
2. 2
   Экстракцияthe product extracted with diethyl ether (3×75 ml)
3. 3
   СушкаThe combined organic fractions were dried over sodium sulphate for 16 h
4. 4
   Фильтрацияfiltered
5. 5
   Другоеthe solvents removed under reduced pressure
6. 6
   Другоеa rotary evaporator
7. 7
   Другоеto yield a brown oil
8. 8
   workup.DISTILLATIONThe crude product was distilled under reduced pressure (b.p. 32°-34° C. at 0.3-0.4 mm Hg)

Методика

To a solution of 26.0 g (101 mmol) tetrahydrofurfuryltosylate prepared according to step (a) above in 200 ml THF cooled to 0° C. was added 63 ml of 2.0M (126 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 then added to the mixture and the product extracted with diethyl ether (3×75 ml). The combined organic fractions were dried over sodium sulphate for 16 h, filtered and the solvents removed under reduced pressure using a rotary evaporator to yield a brown oil. The crude product was distilled under reduced pressure (b.p. 32°-34° C. at 0.3-0.4 mm Hg) to give 7.1 g of a colourless oil (47.3 mmol, 46.9%).

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