Reaction #1458442

Reaction equation

diisobutylaluminum hydride

N-Acetylphenylalanine methyl ester

→

white solid

Yield 74.3%

N-acetylphenylalanine Aldehyde

Yield 74.3%

Solvents

toluene

ethylene glycol dimethyl ether

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   OtherThe reaction is quenched by addition of 2N hydrochloric acid
3. 3
   ExtractionThe mixture is extracted 4 times with cold ethyl acetate and 4 times with toluene
4. 4
   Washwashed with brine
5. 5
   Dryingdried over magnesium sulfate
6. 6
   ConcentrationConcentration in vacuo

Procedure

N-Acetylphenylalanine methyl ester (4.2 g, 19 mmol) is dissolved in ethylene glycol dimethyl ether. The solution is cooled to −70° C. and diisobutylaluminum hydride (25.3 mL of a 1.5M solution in toluene, 39 mmol) is added. The resulting reaction mixture is stirred at −70° C. for 2 hours. The reaction is quenched by addition of 2N hydrochloric acid. The mixture is extracted 4 times with cold ethyl acetate and 4 times with toluene. The extracts are combined, washed with brine and dried over magnesium sulfate. Concentration in vacuo followed by silica gel chromatography furnishes 2.7 g of a white solid. The NMR is as reported in the literature, Biochemistry, 18: 921–926 (1979).

Source