Reaktion #48104

Reaktionsgleichung

sodium chloride

Iodocyclopentane

1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

caesium carbonate

caesium carbonate

iodocyclopentane

→

1-Chloro-2-(4-cyclopentyloxybenzyl)-4-(β-D-glucopyranos-1-yl)-benzene

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONare added
2. 2
   workup.ADDITIONis added
3. 3
   Extraktionthe resulting mixture is extracted with ethyl acetate
4. 4
   TrocknenThe organic phase is dried over sodium sulfate
5. 5
   Sonstigethe solvent is removed
6. 6
   Sonstigethe residue is purified

Vorschrift

0.16 mL Iodocyclopentane are added to a mixture of 0.25 g 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene and 0.4 g caesium carbonate in 2.5 mL of dimethylformamide. The mixture is stirred for 4 h at 45° C., before another 0.1 g caesium carbonate and 0.05 ml iodocyclopentane are added. After another 14 h stirring at 45° C. aqueous sodium chloride solution is added and the resulting mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, the solvent is removed and the residue is purified using silica gel (dichloromethane/methanol 1:0->5:1).

Quelle