Reaction #1375845

Reaction equation

sodium cyclopentadienylide

→

colourless oil

Yield 69.0%

3-butenylcyclopentadiene

Yield 69.0%

Solvents

THF

THF

Conditions

Workup

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

Procedure

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 2.0 M (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%).

Source