I[C:2]1[O:3][CH:4]=[CH:5][CH:6]=1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[CH:15])=[CH:10][CH:9]=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:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:43]=[N:44][N:45]([C:2]3[O:3][CH:4]=[CH:5][CH:6]=3)[CH:15]=2)=[CH:10][CH:9]=1
A sealed tube was charged sequentially with 2-iodofuran (400 mg, 2.061 mmol), 1-chloro-4-ethynylbenzene (280 mg, 2.061 mmol), L-proline (47.4 mg, 0.412 mmol), Na2CO3 (44 mg, 0.412 mmol), sodium ascorbate (82 mg, 0.412 mmol), DMSO-H2O (9:1; 9 ml), NaN3 (160 mg, 2.47 mmol) and CuSO4.5H2O (514 mg, 2.061 mmol). The tube was sealed and stirred at 65° C. for 16 hours. The reaction mixture was then poured into a 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 product, which was purified by column chromatography with 20% ethyl acetate/hexane to yield 4-(4-chlorophenyl)-1-(furan-2-yl)-1H-1,2,3-triazole (6 mg, 1.2%) as a pale yellow solid. The HPLC purity of the final product was 93.6%. LC-MS [M+1] 246 (C12H8ClN3O+H expected 246.04). The 1H-NMR spectra was in accordance with the chemical structure.
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