반응 #2130091

반응 방정식

water

hydrochloric acid

cyanide

2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)acetonitrile

NaOH

→

titled compound 55

수율 98.0%

2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)acetic acid

수율 98.0%

용매

EtOH

반응 조건

후처리

1. 1
   온도The reaction mixture was refluxed overnight
2. 2
   추출extracted with EtOAc
3. 3
   세척The organic layer was washed with water and brine
4. 4
   건조to drying over anhydrous MgSO4
5. 5
   여과Filtration and concentration under reduced pressure

실험 절차

To a solution of cyanide β-39 (53 g, 79 mmol) in EtOH (300 mL) was added aq. NaOH solution (8.0 N, 300 mL, 2.4 mol). The reaction mixture was refluxed overnight. After cooling to room temperature, hydrochloric acid (3.0N) was added to neutralize the reaction mixture. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine prior to drying over anhydrous MgSO4. Filtration and concentration under reduced pressure yielded the titled compound 55 (54 g, 98%) as a white solid.

출처