반응 #1051366

반응 방정식

tetrahydrofurfuryltosylate

sodium cyclopentadienylide

→

colourless oil

수율 46.9%

Tetrahydrofurfurylcyclopentadiene

수율 46.9%

용매

THF

THF

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   추출the product extracted with diethyl ether (3×75 ml)
3. 3
   건조The combined organic fractions were dried over sodium sulphate for 16 h
4. 4
   여과filtered
5. 5
   기타the solvents removed under reduced pressure
6. 6
   기타a rotary evaporator
7. 7
   기타to 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)

실험 절차

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%).

출처