Réaction #1447103

Équation de réaction

sodium hydroxide

1-cyano-3-(4-ethylbenzyl)-2-methyl-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzene

hydrochloric acid

→

1-Cyano-3-(4-ethylbenzyl)-5-(β-D-glucopyranos-1-yl)-2-methyl-benzene

Solvants

methanol

THF

Conditions de réaction

Traitement

1. 1
   AutreAfter removal of the organic solvents
2. 2
   workup.ADDITIONthe residue is diluted with aqueous sodium bicarbonate solution
3. 3
   Extractionthe resulting mixture is extracted with ethyl acetate
4. 4
   SéchageThe combined organic extracts are dried (sodium sulphate)
5. 5
   Autrethe solvent is evaporated
6. 6
   AutreThe remainder is purified by chromatography on silica gel (dichloromethane/methanol 1:0->8:1)

Mode opératoire

Aqueous sodium hydroxide solution (1.7 mL, 4 mol/L) is added to 1-cyano-3-(4-ethylbenzyl)-2-methyl-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzene (0.85 g) dissolved in methanol (6 mL) and THF (3 mL). The solution is stirred at room temperature for 1 h and then neutralized with hydrochloric acid (1 mol/L). After removal of the organic solvents, the residue is diluted with aqueous sodium bicarbonate solution and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are dried (sodium sulphate) and the solvent is evaporated. The remainder is purified by chromatography on silica gel (dichloromethane/methanol 1:0->8:1).

Source