Réaction #48105

Équation de réaction

triethylamine

trimethylsilylacetylene

1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(trifluoromethylsulphonyloxy)-benzyl]-benzene

trimethylsilylacetylene

sodium hydrogen carbonate

→

1-Chloro-2-(4-ethynyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreThe flask is tightly sealed
2. 2
   workup.STIRRINGthe solution is stirred for a further 10 h at 90° C
3. 3
   Extractionthe resultant mixture is extracted three times with ethyl acetate
4. 4
   Séchagethe combined organic phases are dried over sodium sulfate
5. 5
   AutreAfter the solvent has been evaporated
6. 6
   workup.DISSOLUTIONthe residue is dissolved in 5 ml of methanol
7. 7
   workup.STIRRINGThe mixture is stirred for 1 h at ambient temperature
8. 8
   AutreThen the methanol is evaporated off
9. 9
   Extractionextracted with ethyl acetate
10. 10
    AutreThe organic extracts collected
11. 11
    Séchageare dried over sodium sulfate
12. 12
    Autrethe solvent is removed
13. 13
    AutreThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1)

Mode opératoire

25 mg of copper iodide, 44 mg of bis-(triphenylphosphine)-palladium dichloride, 0.30 ml triethylamine and finally 0.14 ml of trimethylsilylacetylene are added under argon to a solution of 0.32 g 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(trifluoromethylsulphonyloxy)-benzyl]-benzene in 3 ml of dimethylformamide. The flask is tightly sealed and the mixture is stirred for 8 h at 90° C. Then another 25 mg of bis-(triphenylphosphine)-palladium dichloride and 0.1 ml trimethylsilylacetylene are added, and the solution is stirred for a further 10 h at 90° C. Then aqueous sodium hydrogen carbonate solution is added, the resultant mixture is extracted three times with ethyl acetate, and the combined organic phases are dried over sodium sulfate. After the solvent has been evaporated, the residue is dissolved in 5 ml of methanol and combined with 0.12 g potassium carbonate. The mixture is stirred for 1 h at ambient temperature and then neutralised with 1 M hydrochloric acid. Then the methanol is evaporated off, the residue is combined with brine and extracted with ethyl acetate. The organic extracts collected are dried over sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1).

Source