Reacción #833571

Ecuación de reacción

4-[(4-methoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole

potassium carbonate

iodomethane

→

4-[(4-methoxyphenyl)methyl]-1,5-dimethyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)pyrazole

Rendimiento 21.7%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction mixture was filtered through Celite®
2. 2
   Otrothe solvent of the filtrate was removed under reduced pressure
3. 3
   OtroThe residue was purified by preparative thin layer chromatography on silica gel (developing solvent: benzene/acetone=2/1)

Procedimiento

A suspension of 4-[(4-methoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (18 mg), potassium carbonate (14 mg) and iodomethane (4.7 mg) in acetonitrile (2 mL) was stirred at 75° C. overnight. The reaction mixture was filtered through Celite®, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (developing solvent: benzene/acetone=2/1) to give 4-[(4-methoxyphenyl)methyl]-1,5-dimethyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)pyrazole (4 mg).

Fuente