Reacción #7467

Ecuación de reacción

4-({4-[3-(benzyloxy)propyl]phenyl}methyl)-5-trifluoromethyl-1,2-dihydro-3H-pyrazole-3-one

acetobromo-α-D-glucose

potassium carbonate

→

4-({4-[3-(benzyloxy)propyl]phenyl}methyl)-5-trifluoromethyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole

Rendimiento 41.8%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroInsoluble materials were removed by filtration
2. 2
   Otrothe solvent of the filtrate was removed under reduced pressure
3. 3
   OtroThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1-1/2)

Procedimiento

To a solution of 4-({4-[3-(benzyloxy)propyl]phenyl}methyl)-5-trifluoromethyl-1,2-dihydro-3H-pyrazole-3-one (0.83 g) and acetobromo-α-D-glucose (1.5 g) in acetonitrile (12 mL) was added potassium carbonate (0.55 g), and the mixture was stirred at 60° C. for 20 hours. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1-1/2) to give 4-({4-[3-(benzyloxy)propyl]phenyl}methyl)-5-trifluoromethyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.64 g).

Fuente