反应 #543554

反应方程式

diisobutylaluminum hydride

N-Cyclohexanoylphenylalanine methyl ester

→

N-cyclohexanoylphenylalanine Aldehyde

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 dropwise addition of 2N hydrochloric acid
3. 3
   萃取The mixture is extracted with cold ethyl acetate
4. 4
   洗涤The ethyl acetate solution is washed with brine
5. 5
   干燥dried over sodium sulfate
6. 6
   浓缩Concentration in vacuo
7. 7
   其他furnishes a white solid, which
8. 8
   其他is purified by silica gel chromatography

实验过程

N-Cyclohexanoylphenylalanine methyl ester (0.5 g) is dissolved in ethylene glycol dimethyl ether (20 mL). The solution is cooled to 70° C. and diisobutylaluminum hydride (2.04 mL of a 1.5M solution in toluene) is added. The resulting reaction mixture is stirred at −70° C. for 2 hours. The reaction is quenched by dropwise addition of 2N hydrochloric acid. The mixture is extracted with cold ethyl acetate. The ethyl acetate solution is washed with brine and dried over sodium sulfate. Concentration in vacuo furnishes a white solid, which is purified by silica gel chromatography. 1H NMR (300 MHz, DMSO-d6): 9.5 (s, 1H), 8.2 (d, 1H), 7.2 (m, 5H), 4.2 (m, 1H), 3.2 (d, 1H), 2.7 (d, 1H), 2.1 (m, 1H), 1.6 (br.m, 4H), 1.2 (br.m, 6H). R (KBr): 3300, 3050, 2900, 2850, 2800, 1700, 1600, 1500 cm−1. Mass Spec.: M+1 m/e 261.

来源