Reaktion #1909786

Reaktionsgleichung

L-phenylalaninol

sodium hydride

benzyl bromide

→

title compound

Ausbeute 77.0%

O-Benzyl-L-phenylalaninol

Ausbeute 77.0%

Lösungsmittel

THF

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   TemperaturTwenty minutes later, the reaction mixture was refluxed
3. 3
   Temperaturunder heating for 1 hour
4. 4
   Temperaturto cool
5. 5
   Temperaturcooling
6. 6
   Extraktionextracted with ether
7. 7
   ExtraktionThe organic layer was extracted with 10% hydrochloric acid
8. 8
   Extraktionextracted with ether
9. 9
   WaschenThe organic layer was washed with saturated brine
10. 10
    Trocknendried over anhydrous magnesium sulfate
11. 11
    Einengenconcentrated under reduced pressure

Vorschrift

To a solution of L-phenylalaninol (11.78 g) in THF (200 ml) was gradually added 60% sodium hydride (3.43 g) in oil at room temperature. Twenty minutes later, the reaction mixture was refluxed under heating for 1 hour. Then, the mixture was allowed to cool, followed by gradual addition of benzyl bromide (9.27 ml) under ice-cooling, and stirred at room temperature for 16 hours. The reaction mixture was added to saturated brine, and extracted with ether. The organic layer was extracted with 10% hydrochloric acid. The aqueous layer was made alkaline with an aqueous sodium hydroxide solution, and extracted with ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (14.5 g, yield 77%).

Quelle