Reaktion #1447103

Reaktionsgleichung

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

Lösungsmittel

methanol

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter removal of the organic solvents
2. 2
   workup.ADDITIONthe residue is diluted with aqueous sodium bicarbonate solution
3. 3
   Extraktionthe resulting mixture is extracted with ethyl acetate
4. 4
   TrocknenThe combined organic extracts are dried (sodium sulphate)
5. 5
   Sonstigethe solvent is evaporated
6. 6
   SonstigeThe remainder is purified by chromatography on silica gel (dichloromethane/methanol 1:0->8:1)

Vorschrift

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).

Quelle