反応 #61393

反応方程式

Water

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

acetobromo-α-D-glucose

potassium carbonate

→

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

収率 46.6%

溶媒

acetonitrile

反応条件

後処理

1. 1
   抽出the resulting mixture was extracted with ethyl acetate
2. 2
   洗浄The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他The solvent was removed under reduced pressure
5. 5
   その他the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1)

実験手順

To a solution of 1,2-dihydro-4-[(4-methylthiophenyl)-methyl]-5-trifluoromethyl-3H-pyrazol-3-one (2.0 g) in acetonitrile (100 mL) were added acetobromo-α-D-glucose (3.1 g) and potassium carbonate (1.1 g), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1) to give 4-[(4-methylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole (2.0 g).

出典