Reaktion #1051366

Reaktionsgleichung

tetrahydrofurfuryltosylate

sodium cyclopentadienylide

→

colourless oil

Ausbeute 46.9%

Tetrahydrofurfurylcyclopentadiene

Ausbeute 46.9%

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 h
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. 32°-34° C. at 0.3-0.4 mm Hg)

Vorschrift

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%).

Quelle