Reaction #1914840

Reaction equation

Water

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

cesium carbonate

iodopropane

→

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

Solvents

N,N-dimethylformamide

Conditions

Workup

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

Procedure

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 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