Réaction #1909786

Équation de réaction

L-phenylalaninol

sodium hydride

benzyl bromide

→

title compound

Rendement 77.0%

O-Benzyl-L-phenylalaninol

Rendement 77.0%

Solvants

THF

brine

Conditions de réaction

Traitement

1. 1
   Autreat room temperature
2. 2
   TempératureTwenty minutes later, the reaction mixture was refluxed
3. 3
   Températureunder heating for 1 hour
4. 4
   Températureto cool
5. 5
   Températurecooling
6. 6
   Extractionextracted with ether
7. 7
   ExtractionThe organic layer was extracted with 10% hydrochloric acid
8. 8
   Extractionextracted with ether
9. 9
   LavageThe organic layer was washed with saturated brine
10. 10
    Séchagedried over anhydrous magnesium sulfate
11. 11
    Concentrationconcentrated under reduced pressure

Mode opératoire

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%).

Source