Reaction #1447103

Reaction equation

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

Solvents

methanol

THF

Conditions

Workup

1. 1
   OtherAfter 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
   DryingThe combined organic extracts are dried (sodium sulphate)
5. 5
   Otherthe solvent is evaporated
6. 6
   OtherThe remainder is purified by chromatography on silica gel (dichloromethane/methanol 1:0->8:1)

Procedure

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