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Synthesis of 4-(4-Methoxyphenyl)-5-[2-(4-methoxyphenyl)ethynyl]-1- phenyl-1H-1,2,3-triazole (4a, Typical Procedure: A mixture of 1a (50.0 mg, 0.41 mmol, 2a (118.9 mg, 0.90 mmol, sodium azide (3; 40.3 mg, 0.62 mmol, CuI (7.8 mg, 0.041 mmol) and CuSO 4·5H2O (20.5 mg, 0.082 mmol) in 1,4-dioxane (10 mL) and H2O (5 mL) was stirred overnight. Then, the reaction mixture was diluted with H2O (20 mL) and was extracted with CH 2Cl2 (3 x 20 mL, The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography (PE-EtOAc, 10:1) to afford 4a (98.5 mg, 63, as a white solid; mp 86-88°C. IR (KBr, 2216 cm-1. 1H NMR (300 MHz, CDCl3, δ, 3.83 (s, 3 H, 3.87 (s, 3 H, 6.89 (d, J, 9.3 Hz, 2 H, 7.03 (d, J, 8.7 Hz, 2 H, 7.40 d, J, 8.7 Hz
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3): δ = 2.67 (s, 3 H), 3.84 (s, 3 H), 3.87 (s, 3 H), 6.91
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(a) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2632.
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-1, F(000) = 672.0. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-626008.
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-1, F(000) = 672.0. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-626008.
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