Reaction #1447104

Reaction equation

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

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureAfter cooling to ambient temperature
2. 2
   OtherAfter removal of the organic solvents
3. 3
   Extractionthe residue is extracted with ethyl acetate
4. 4
   Dryingthe combined organic extracts are dried (sodium sulphate)
5. 5
   Otherthe solvent is evaporated
6. 6
   OtherThe remainder is purified by HPLC on reversed phase (YMC C18, acetonitrile/water)

Procedure

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