Reaktion #48115

Reaktionsgleichung

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

pentafluoroethyltrimethylsilane

KF

NaHCO3

→

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

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture is extracted with ethyl acetate
2. 2
   TrocknenThe combined organic phases are dried over sodium sulfate
3. 3
   Sonstigethe solvent is removed
4. 4
   workup.DISSOLUTIONThe residue is dissolved in methanol (8 mL)
5. 5
   workup.ADDITIONtreated with 4 M KOH solution (0.8 mL)
6. 6
   workup.ADDITIONdiluted with aqueous NaHCO3 solution
7. 7
   SonstigeAfter removal of the methanol under reduced pressure
8. 8
   Extraktionthe residue is extracted with ethyl acetate
9. 9
   Sonstigethe combined organic extracts are dried
10. 10
    Sonstigethe solvent is removed
11. 11
    SonstigeThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1)

Vorschrift

A flask charged with 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile (0.16 g), pentafluoroethyltrimethylsilane (0.14 g), KF (43 mg), CuI (0.16 g), DMF (2 mL) and Ar atmosphere is heated at 60° C. for 24 h. Then, aqueous NaHCO3 solution is added and the resulting mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is dissolved in methanol (8 mL) and treated with 4 M KOH solution (0.8 mL). The solution is stirred at room temperature for 1 h and then diluted with aqueous NaHCO3 solution. After removal of the methanol under reduced pressure, the residue is extracted with ethyl acetate, the combined organic extracts are dried and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1).

Quelle