Reaction #1909786

Reaction equation

L-phenylalaninol

sodium hydride

benzyl bromide

→

title compound

Yield 77.0%

O-Benzyl-L-phenylalaninol

Yield 77.0%

Solvents

THF

brine

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   TemperatureTwenty minutes later, the reaction mixture was refluxed
3. 3
   Temperatureunder heating for 1 hour
4. 4
   Temperatureto cool
5. 5
   Temperaturecooling
6. 6
   Extractionextracted with ether
7. 7
   ExtractionThe organic layer was extracted with 10% hydrochloric acid
8. 8
   Extractionextracted with ether
9. 9
   WashThe organic layer was washed with saturated brine
10. 10
    Dryingdried over anhydrous magnesium sulfate
11. 11
    Concentrationconcentrated under reduced pressure

Procedure

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