反应 #48112

反应方程式

2-bromomethyl-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzonitrile

4-trifluoromethoxy-phenylboronic acid

potassium carbonate

acetone

→

4-(β-D-glucopyranos-1-yl)-2-(4-trifluoromethoxy-benzyl)-benzonitrile

溶剂

water

brine

反应条件

后处理

1. 1
   workup.ADDITIONAn Ar filled flask
2. 2
   温度is cooled in an ice-bath
3. 3
   workup.STIRRINGthe reaction mixture is stirred for 16 h at ambient temperature
4. 4
   萃取extracted with ethyl acetate
5. 5
   干燥The combined extracts are dried over sodium sulfate
6. 6
   其他the solvent is removed under reduced pressure
7. 7
   workup.DISSOLUTIONThe residue is dissolved in methanol (9 mL)
8. 8
   workup.ADDITIONtreated with 4 M aqueous potassium hydroxide solution (1 mL)
9. 9
   workup.STIRRINGThe resulting solution is stirred at ambient temperature for 1 h
10. 10
    其他The methanol is evaporated
11. 11
    workup.ADDITIONthe residue is diluted with brine
12. 12
    萃取extracted with ethyl acetate
13. 13
    其他The organic extracts collected
14. 14
    干燥are dried over sodium sulfate
15. 15
    其他the solvent is removed
16. 16
    其他The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1)

实验过程

An Ar filled flask is charged with 2-bromomethyl-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzonitrile (0.25 g), 4-trifluoromethoxy-phenylboronic acid (0.20 g), potassium carbonate (0.26) and a 3:1 mixture of degassed acetone and water (4 mL). The mixture is stirred at room temperature for 5 min, before it is cooled in an ice-bath. Then palladium dichloride (5 mg) is added and the reaction mixture is stirred for 16 h at ambient temperature. The mixture is then diluted with brine and extracted with ethyl acetate. The combined extracts are dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is dissolved in methanol (9 mL) and treated with 4 M aqueous potassium hydroxide solution (1 mL). The resulting solution is stirred at ambient temperature for 1 h and then neutralized with 1 M hydrochloric acid. The methanol is evaporated, and the residue is diluted with brine and extracted with ethyl acetate. The organic extracts collected are dried over sodium sulfate, and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1).

来源