Reaktion #456857

Reaktionsgleichung

3-chloro-1-propene

1,5-pentanediol

sodium hydride

hydrogen

→

5-(3-chloro-1-propenyloxy)pentanol

Ausbeute 21.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise under ice cooling
2. 2
   TemperaturThe reaction mixture was slowly warmed
3. 3
   Extraktionextracted twice with diethyl ether
4. 4
   Waschenwashed with water
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto give a crude product

Vorschrift

In a reaction vessel containing 10.42 g of 1,5-pentanediol was put 2.20 g of 60% sodium hydride (in oil), and the mixture was stirred until the evolution of hydrogen gas ceased, to which 3.83 g of 3-chloro-1-propene was added dropwise under ice cooling. The reaction mixture was slowly warmed and stirred at 60° C. for 3 hours, which was then poured into water and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 1.50 g of 5-(3-chloro-1-propenyloxy)pentanol (yield, 21%).

Quelle