Reaktionsgleichung
[C:1]([C:3]1[O:4][CH:5]=[CH:6][CH:7]=1)#[CH:2].[Cl:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1.N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[Na+].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[N-:43]=[N+:44]=[N-:45].[Na+].[OH-].[NH4+]>CS(C)=O.O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:43]2[CH:2]=[C:1]([C:3]3[O:4][CH:5]=[CH:6][CH:7]=3)[N:45]=[N:44]2)=[CH:11][CH:10]=1Komponenten
Edukt 7
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
A sealed tube was charged sequentially with 2-ethynylfuran (153 mg, 1.663 mmol), 1-chloro-4-iodobenzene (395 mg, 1.663 mmol), L-proline (38.2 mg, 0.332 mmol), Na2CO3 (35 mg, 0.332 mmol), sodium ascorbate (66 mg, 0.332 mmol), DMSO-H2O (9:1; 7 ml), NaN3 (130 mg, 1.99 mmol) and CuSO4.5H2O (415 mg, 1.663 mmol). The tube was sealed and stirred at 65° C. for 16 hours. The reaction mixture was poured onto cold ammonium hydroxide solution, and the mixture was extracted with ethyl acetate (3×30 ml). The combined organic layers were washed with brine solution (30 ml), dried over sodium sulfate and evaporated to yield the crude material, which was purified by column chromatography with 20% ethyl acetate/hexane yielding 1-(4-chlorophenyl)-4-(furan-2-yl)-1H-1,2,3-triazole (20 mg, yield 4.9%) as a pale yellow solid. The HPLC purity was 98.02%. LC-MS [M+H] 246 (C12H8ClN3O+H, expected 246.04). The 1H-NMR spectra was in accordance with the chemical structure.
Aufarbeitung
- customThe tube was sealed
- extractionthe mixture was extracted with ethyl acetate (3×30 ml)
- washThe combined organic layers were washed with brine solution (30 ml)
- dry with materialdried over sodium sulfate
- customevaporated
- customto yield the crude material, which
- customwas purified by column chromatography with 20% ethyl acetate/hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-5e21d91017a446c9a43e1b14ba0fb3de
- Quelldatensatz
- uspto-grants-2016_08
- Patentnummer
- US09402397B2
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