반응 #48105

반응 방정식

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

용매

dimethylformamide

반응 조건

후처리

1. 1
   기타The flask is tightly sealed
2. 2
   workup.STIRRINGthe solution is stirred for a further 10 h at 90° C
3. 3
   추출the resultant mixture is extracted three times with ethyl acetate
4. 4
   건조the combined organic phases are dried over sodium sulfate
5. 5
   기타After 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
   기타Then the methanol is evaporated off
9. 9
   추출extracted with ethyl acetate
10. 10
    기타The organic extracts collected
11. 11
    건조are dried over sodium sulfate
12. 12
    기타the solvent is removed
13. 13
    기타The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1)

실험 절차

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).

출처