Reaktion #411013

Reaktionsgleichung

1-bromooctane

sodium cyclopentadienide

water

diethyl ether

→

n-octylcyclopentadiene

Ausbeute 79.0%

Lösungsmittel

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle