Azidotrimethylsilane → 2-Chloro-5-(2H-[1,2,3]triazol-4-yl)-benzoic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:10]#[CH:11])[CH:7]=[CH:6][C:5]=1[Cl:12].C[Si]([N:18]=[N+:19]=[N-:20])(C)C>C(O)CCC>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:20][NH:19][N:18]=2)[CH:7]=[CH:6][C:5]=1[Cl:12]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 2-chloro-5-ethynyl-benzoic acid methyl ester (0.18 g, 0.92 mmol) and trimethylsilyl azide (0.16 g, 1.39 mmol) in n-butanol was heated to reflux for 16 h. A second portion of trimethylsilyl azide (0.16 g, 1.39 mmol) was added and the mixture was refluxed for a further 16 h. A third portion of trimethylsilyl azide (0.16 g, 1.39 mmol) was added and the mixture was refluxed for a further 16 h. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by flash column chromatography (2:1 hexanes-ethyl acetate) to afford the title compound (0.095 g).