反应 #543555

反应方程式

diisobutylaluminum hydride

N-Acetylphenylalanine methyl ester

→

white solid

收率 74.3%

N-acetylphenylalanine Aldehyde

收率 74.3%

溶剂

toluene

ethylene glycol dimethyl ether

反应条件

后处理

1. 1
   其他The resulting reaction mixture
2. 2
   其他The reaction is quenched by addition of 2N hydrochloric acid
3. 3
   萃取The mixture is extracted 4 times with cold ethyl acetate and 4 times with toluene
4. 4
   洗涤washed with brine
5. 5
   干燥dried over magnesium sulfate
6. 6
   浓缩Concentration in vacuo

实验过程

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).

来源