反応 #6737

反応方程式

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

収率 39.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他at 65° C.
2. 2
   その他overnight
3. 3
   その他The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran)
4. 4
   その他Further purification by preparative thin layer chromatography on silica gel (developing solvent: ethyl acetate/hexane=2/1)

実験手順

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).

出典