تفاعل #1051366

معادلة التفاعل

tetrahydrofurfuryltosylate

sodium cyclopentadienylide

→

colourless oil

المردود 46.9%

Tetrahydrofurfurylcyclopentadiene

المردود 46.9%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to room temperature
2. 2
   استخلاصthe product extracted with diethyl ether (3×75 ml)
3. 3
   تجفيفThe combined organic fractions were dried over sodium sulphate for 16 h
4. 4
   ترشيحfiltered
5. 5
   أخرىthe solvents removed under reduced pressure
6. 6
   أخرىa rotary evaporator
7. 7
   أخرىto 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)

الإجراء التجريبي

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%).

المصدر