Reacción #48104

Ecuación de reacción

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

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente