反応 #7488

反応方程式

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

溶媒

Water

N,N-dimethylformamide

反応条件

後処理

1. 1
   抽出the mixture was extracted with ethyl acetate
2. 2
   洗浄The organic layer was washed with water
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: dichloromethane/methanol=10/1-8/1)

実験手順

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).

出典