تفاعل #948477

معادلة التفاعل

sodium cyclopentadienylide

→

3-butenylcyclopentadiene

المردود 69.0%

colourless oil

المردود 69.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر