Reacción #1447104

Ecuación de reacción

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

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to ambient temperature
2. 2
   OtroAfter removal of the organic solvents
3. 3
   Extracciónthe residue is extracted with ethyl acetate
4. 4
   Secadothe combined organic extracts are dried (sodium sulphate)
5. 5
   Otrothe solvent is evaporated
6. 6
   OtroThe remainder is purified by HPLC on reversed phase (YMC C18, acetonitrile/water)

Procedimiento

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).

Fuente