Reaction #6737

Reaction equation

1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one

acetobromo-α-D-glucose

→

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

Yield 39.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherat 65° C.
2. 2
   Otherovernight
3. 3
   OtherThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran)
4. 4
   OtherFurther purification by preparative thin layer chromatography on silica gel (developing solvent: ethyl acetate/hexane=2/1)

Procedure

To a suspension of 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one (46 mg), acetobromo-α-D-glucose (99 mg) and 4A molecular sieves in tetrahydrofuran (3 mL) was added silver carbonate (66 mg), and the mixture was stirred under shading the light at 65° C. overnight. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran). Further purification by preparative thin layer chromatography on silica gel (developing solvent: ethyl acetate/hexane=2/1) afforded 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (42 mg).

Source