Reaktion #1051365

Reaktionsgleichung

2-methoxyethyltosylate

sodium cyclopentadienylide

→

colourless oil

Ausbeute 44.0%

2-methoxyethylcyclopentadiene

Ausbeute 44.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   Extraktionthe product extracted with diethyl ether (3×75 ml)
3. 3
   TrocknenThe combined organic fractions were dried over sodium sulphate for 16 hrs
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvents removed under reduced pressure
6. 6
   Sonstigea rotary evaporator
7. 7
   Sonstigeto 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)

Vorschrift

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%).

Quelle