Reaction #1051365

Reaction equation

2-methoxyethyltosylate

sodium cyclopentadienylide

→

colourless oil

Yield 44.0%

2-methoxyethylcyclopentadiene

Yield 44.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   Extractionthe product extracted with diethyl ether (3×75 ml)
3. 3
   DryingThe combined organic fractions were dried over sodium sulphate for 16 hrs
4. 4
   Filtrationfiltered
5. 5
   Otherthe solvents removed under reduced pressure
6. 6
   Othera rotary evaporator
7. 7
   Otherto yield a brown oil
8. 8
   workup.DISTILLATIONThe crude product was distilled under reduced pressure (b.p. 40°-44° C. at 2-3 mm Hg)

Procedure

To a solution of 19.7 g(85.7 mmol) 2-methoxyethyltosylate as prepared in step (a) in 200 ml THF cooled to 0° C. was added 55 ml of 2.0M (110 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 diethyl ether (3×75 ml). The combined organic fractions were dried over sodium sulphate for 16 hrs, 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. 40°-44° C. at 2-3 mm Hg) to give 4.5 g of a colourless oil (37.7 mmol, 44.0%).

Source