反応 #48112

反応方程式

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

溶媒

water

brine

反応条件

後処理

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
   抽出extracted with ethyl acetate
5. 5
   乾燥The combined extracts are dried over sodium sulfate
6. 6
   その他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
    その他The methanol is evaporated
11. 11
    workup.ADDITIONthe residue is diluted with brine
12. 12
    抽出extracted with ethyl acetate
13. 13
    その他The organic extracts collected
14. 14
    乾燥are dried over sodium sulfate
15. 15
    その他the solvent is removed
16. 16
    その他The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1)

実験手順

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).

出典