Реакция #411013

Уравнение реакции

1-bromooctane

sodium cyclopentadienide

water

diethyl ether

→

n-octylcyclopentadiene

Выход 79.0%

Растворители

tetrahydrofuran

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   ДругоеThe diethyl ether layer was separated
3. 3
   Сушкаdried over anhydrous magnesium sulfate
4. 4
   ДругоеAfter removing magnesium sulfate
5. 5
   workup.DISTILLATIONthe organic solvent was distilled off under a reduced pressure

Методика

Under a high purity nitrogen atmosphere, 5.8 ml(30mmol) of 1-bromooctane was introduced into a Schlenck flask and 50 ml of tetrahydrofuran (THF) was added thereto. To the resulting mixture, 18 ml of 2N sodium cyclopentadienide in THF was added at 0° C. The resultant was stirred for 5 hours at room temperature, 100 ml of water and 100 ml of diethyl ether were added thereto, followed by agitation. The diethyl ether layer was separated and dried over anhydrous magnesium sulfate. After removing magnesium sulfate, the organic solvent was distilled off under a reduced pressure and the residue was subjected to silica gel column chromatography (eluent: hexane) to obtain 4.21 g of n-octylcyclopentadiene (yield: 79%).

Источник