Reacción #1447103

Ecuación de reacción

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

Disolventes

methanol

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter removal of the organic solvents
2. 2
   workup.ADDITIONthe residue is diluted with aqueous sodium bicarbonate solution
3. 3
   Extracciónthe resulting mixture 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 chromatography on silica gel (dichloromethane/methanol 1:0->8:1)

Procedimiento

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).

Fuente