Réaction #1447104

Équation de réaction

hydrochloric acid

6-(4-ethylbenzyl)-2-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzonitrile

pyridinium hydrochloride

NaOH

→

6-(4-Ethylbenzyl)-4-(β-D-glucopyranos-1-yl)-2-hydroxy-benzonitrile

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to ambient temperature
2. 2
   AutreAfter removal of the organic solvents
3. 3
   Extractionthe residue 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 HPLC on reversed phase (YMC C18, acetonitrile/water)

Mode opératoire

A mixture of 6-(4-ethylbenzyl)-2-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzonitrile (0.36 g) and pyridinium hydrochloride (0.72 g) is heated at 215° C. for 1.5 h. After cooling to ambient temperature, the mixture is dissolved in methanol (8 mL) and treated with 4 M aqueous NaOH solution (2.5 mL). The solution is stirred at room temperature for 1 h and then acidified using hydrochloric acid (4 mol/L). After removal of the organic solvents, the residue is extracted with ethyl acetate, the combined organic extracts are dried (sodium sulphate) and the solvent is evaporated. The remainder is purified by HPLC on reversed phase (YMC C18, acetonitrile/water).

Source