Reacción #7488

Ecuación de reacción

sodium iodide

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

cesium carbonate

bromomethylcyclopropane

→

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

Disolventes

Water

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with ethyl acetate
2. 2
   LavadoThe organic layer was washed with water
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Otrothe solvent was removed under reduced pressure
5. 5
   OtroThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-8/1)

Procedimiento

To a solution of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.081 g) in N,N-dimethylformamide (1 mL) were added cesium carbonate (0.40 g), bromomethylcyclopropane (0.099 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 7 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-8/1) to give 1-(cyclopropylmethyl)-3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4methylthiophenyl)methyl]-1H-pyrazole (0.041 g).

Fuente