Réaction #6747

Équation de réaction

Water

3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole

cesium carbonate

1-iodopropane

→

3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1-propylpyrazole

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONthe resulting mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)
2. 2
   AutreThe resulting semi-purified material was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=8/1)

Mode opératoire

To a suspension of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (50 mg) and cesium carbonate (0.20 g) in N,N-dimethylformamide (1 mL) was added 1-iodopropane (0.036 mL) at 50° C., and the mixture was stirred overnight. Water was added to the reaction mixture, and the resulting mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol). The resulting semi-purified material was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=8/1) to give 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1-propylpyrazole (28 mg).

Source