Reaktion #64429

Reaktionsgleichung

1-bromo-5-benzyloxy pentane

t-butyl lithium

3-bromo-(1-hexenyl)benzene

→

3-(5-benzyloxypentyl)-1-(1-hexenyl)benzene

Lösungsmittel

hexane

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITto come to ambient temperature over 5 hours
2. 2
   workup.STIRRINGstirring for an additional 24 hours
3. 3
   workup.ADDITIONsilica gel is added
4. 4
   Einengenand the mixture is concentrated
5. 5
   Sonstigechromatographed (HPLC)

Vorschrift

At -78° C., 27.8 ml of t-butyl lithium (1.7M) in hexane are added to 5.30 gm of 3-bromo-(1-hexenyl)benzene in 75 mls of tetrahydrofuran. The reaction is stirred for 10 minutes, and then 1.1 ml of Li2CuCl3 (0.20M/THF) is added followed dropwise by 5.78 grams of 1-bromo-5-benzyloxy pentane. After allowing the reaction mixture to come to ambient temperature over 5 hours and stirring for an additional 24 hours, silica gel is added; and the mixture is concentrated and then chromatographed (HPLC) to yield pure 3-(5-benzyloxypentyl)-1-(1-hexenyl)benzene.

Quelle