Reaktion #7895

Reaktionsgleichung

sodium hydride

1,4-butanediol

benzyl bromide

HCl

→

title compound

Ausbeute 48.0%

4-benzyloxybutanol

Ausbeute 48.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto stand at room temperature
2. 2
   workup.ADDITIONwas added dropwise to the reaction mixture at room temperature
3. 3
   Extraktionthe reaction mixture was extracted with diethyl ether
4. 4
   WaschenAfter the organic layer was washed with an aqueous solution of sodium hydrogen carbonate
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   SonstigeThe resulting residue was purified by silica gel column chromatography

Vorschrift

While a suspension containing 2.5 g of 60% sodium hydride was in 50 ml of tetrahydrofuran was allowed to stand at room temperature, 5.7 g of 1,4-butanediol was slowly added dropwise thereto. Then, a solution containing 7.5 ml of benzyl bromide in 20 ml of tetrahydrofuran was added dropwise to the reaction mixture at room temperature, followed by stirring at the same temperature for 2 hours. After the addition of a 10% aqueous solution of HCl, the reaction mixture was extracted with diethyl ether. After the organic layer was washed with an aqueous solution of sodium hydrogen carbonate and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using 150 g of silica gel [with an elution solvent comprising hexane-ethyl acetate (4:1)]. Thus, 5.5 g (48% yield) of the title compound was obtained.

Quelle