反応 #1051366

反応方程式

tetrahydrofurfuryltosylate

sodium cyclopentadienylide

→

colourless oil

収率 46.9%

Tetrahydrofurfurylcyclopentadiene

収率 46.9%

溶媒

THF

THF

反応条件

後処理

1. 1
   温度to warm to room temperature
2. 2
   抽出the product extracted with diethyl ether (3×75 ml)
3. 3
   乾燥The combined organic fractions were dried over sodium sulphate for 16 h
4. 4
   ろ過filtered
5. 5
   その他the solvents removed under reduced pressure
6. 6
   その他a rotary evaporator
7. 7
   その他to 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)

実験手順

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%).

出典