反应 #632069

反应方程式

4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carboxaldehyde

4-(difluoromethoxy)benzeneboronic acid

1,2-dimethoxyethane

→

4-(difluoromethoxy)phenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indol-3-yl methanol

溶剂

H2O

water

反应条件

后处理

1. 1
   萃取The mixture was extracted with ethyl acetate (20 ml) 3 times
2. 2
   干燥the combined organic layer was dried over magnesium sulfate
3. 3
   过滤by being filtered through an aminosilane-
4. 4
   workup.ADDITIONtreated silica gel pad
5. 5
   其他The filtrate was evaporated under reduced pressure

实验过程

A mixture solution of 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carboxaldehyde (350 mg) obtained in Example 25-(1), 4-(difluoromethoxy)benzeneboronic acid (399 mg), (acetylacetonato)dicarbonylrhodium(I) (37 mg) and 1,1′-bis-(diphenylphosphino)ferrocene (79 mg) in H2O (3.6 ml)-1,2-dimethoxyethane (3.6 ml) was stirred at 80° C. under argon atmosphere for 18 hours. The reaction mixture was cooled to room temperature, and thereto was added water (10 ml). The mixture was extracted with ethyl acetate (20 ml) 3 times, and the combined organic layer was dried over magnesium sulfate followed by being filtered through an aminosilane-treated silica gel pad. The filtrate was evaporated under reduced pressure to give crude 4-(difluoromethoxy)phenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indol-3-yl methanol, which was used in the subsequent step without further purification.

来源