反応 #411013

反応方程式

1-bromooctane

sodium cyclopentadienide

water

diethyl ether

→

n-octylcyclopentadiene

収率 79.0%

溶媒

tetrahydrofuran

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The diethyl ether layer was separated
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他After removing magnesium sulfate
5. 5
   workup.DISTILLATIONthe organic solvent was distilled off under a reduced pressure

実験手順

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%).

出典