Reacción #1909786

Ecuación de reacción

L-phenylalaninol

sodium hydride

benzyl bromide

→

title compound

Rendimiento 77.0%

O-Benzyl-L-phenylalaninol

Rendimiento 77.0%

Disolventes

THF

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   TemperaturaTwenty minutes later, the reaction mixture was refluxed
3. 3
   Temperaturaunder heating for 1 hour
4. 4
   Temperaturato cool
5. 5
   Temperaturacooling
6. 6
   Extracciónextracted with ether
7. 7
   ExtracciónThe organic layer was extracted with 10% hydrochloric acid
8. 8
   Extracciónextracted with ether
9. 9
   LavadoThe organic layer was washed with saturated brine
10. 10
    Secadodried over anhydrous magnesium sulfate
11. 11
    Concentraciónconcentrated under reduced pressure

Procedimiento

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%).

Fuente