4.1.8. Experimental Procedure for the Deprotection of Triazole Derivates
CF3COOH (0,08 mL/mmol) was added dropwise to a solution of the corresponding triazole derivative (1 eq) in MeOH (18,2 mL/mmol). The mixture was stirred at room temperature under a nitrogen atmosphere for 30 min. Then, a NaHCO3 aqueous solution (2,7 eq) was added to the mixture. After filtration and evaporation of the solvent, the residue was purified by column chromatography on silica gel as the stationary phase and a mixture of Hexanes:AcOEt (6:4, 1.1, 3:4) as the eluent, affording compounds 2, 4, 6, 8, 10, 11 and 14.
1-bromo-4-ethynylbenzene 21: yield 42%; white solid; m.p. 74.5–75.0 °C; 1H NMR (400 MHz, DMSO-d6) δ 7.59 (d, J = 8.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H), 4.29 (s, 1H); 13C NMR (100 MHz, DMSO-d6); δ 133.60 (2xCH), 131.71 (2xCH), 122.38 (C), 120.92 (C), 82.34 (C), 82.06 (CH).
1-bromo-3-ethynylbenzene 22: yield 53%; colorless liquid; 1H NMR (400 MHz, DMSO-d6) δ 7.68 (s, J = 6.1 Hz, 1H), 7.63 (d, J = 7.7 Hz, 1H), 7.49 (dt, J = 7.9 Hz, J = 1.2 Hz, 1H), 7.35 (t, J = 7.9 Hz, 1H), 4.32 (s, 1H); 13C NMR (100 MHz, DMSO-d6); δ 133.90 (CH), 132.01 (CH), 130.76 (CH), 130.72 (CH), 123.90 (C), 121.56 (C), 82.29 (C), 81.77 (CH).
1-bromo-2-ethynylbenzene 23: yield 67%; colorless liquid; 1H NMR (400 MHz, DMSO-d6) δ 7.71 (dd, J = 7.9 Hz, J = 1.2 Hz, 1H), 7.60 (dd, J = 7.6 Hz, J = 1.8 Hz, 1H), 7.41 (dt, J = 7.5 Hz, J = 1.3 Hz, 1H), 7.35 (dt, J = 7.7 Hz, J = 1.8 Hz, 1H), 4.55 (s, 1H); 13C NMR (100 MHz, DMSO-d6); δ 133.98 (CH), 132.42 (CH), 130.65 (CH), 127.75 (CH), 124.69 (C), 123.59 (C), 85.36 (C), 81.71 (CH).
1-ethynyl-4-methoxybenzene 24: yield 40%; white solid; colorless liquid; 1H NMR (400 MHz, DMSO-d6) δ 7.41 (d, J = 8.9 Hz, 2H), 6.93 (d, J = 8.9 Hz, 2H), 3.99 (s,1H), 3.77 (s,3H); 13C NMR (100 MHz, DMSO-d6) δ 159.57 (C), 133.17 (2xCH), 114.25 (2xCH), 113.64 (C), 83.48 (C), 79.08 (CH), 55.21 (CH3).
1-ethynyl-3-methoxybenzene 25: yield 57%; colorless liquid; 1H NMR (400 MHz, DMSO-d6) δ 7.29 (t, J = 7.9 Hz, 1H), 7.05 (dt, J = 7.5 Hz, J = 1.1 Hz, 1H), 7.00–6.95 (m, 2H), 4.15 (s,1H), 3.76 (s,3H); 13C NMR (100 MHz, DMSO-d6) δ 159.09 (C), 129.81 (CH), 124.00 (CH), 122.76 (C), 116.53 (CH), 115.35 (CH), 83.35 (C), 79.52 (CH), 55.18 (CH3).
1-ethynyl-2-methoxybenzene 26: yield 52%; white solid; colorless liquid; 1H NMR (400 MHz, DMSO-d6) δ 7.40 (dt, J = 7.5 Hz, J = 2.1 Hz, 1H), 7.36 (dd, J = 7.1 Hz, J = 1.3 Hz,1H), 7.05 (d, J = 8.1 Hz, 1H), 6.93 (dt, J = 7.5 Hz, J = 1.0 Hz, 1H), 4.20 (s,1H), 3.81 (s,3H);13C NMR (100 MHz, DMSO-d6) δ 160.21 (C), 133.44 (CH), 130.42 (CH), 120.34 (CH), 111.29 (CH), 110.69 (C), 84.36 (C), 80.13 (CH), 55.51 (CH3).
2,2′-(1,4-phenylene)bis(ethan-1-ol) 16: yield 97%; white solid; m.p. 75–82 °C; 1H NMR (400 MHz, MeOH-d4); δ 7.14 (s, 4H), 4.77 (s, 2H), 3.72 (t, J = 7.1 Hz, 4H), 2.78 (t, J = 7.1 Hz, 4H); 13C NMR (100 MHz, MeOH-d4) δ 138.1 (2xC), 129.9 (2xCH), 64.3 (2xCH2), 39.8 (2xCH2).
2-(4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)phenyl)ethan-1-ol 17: yield 35%; yellow oil; 1H NMR (400 MHz, DMSO-d6) δ 7.30–7.07 (m, 13H), 6.85 (d, J = 8.9 Hz, 4H), 4.58 (t, J = 5.2 Hz, 1H), 3.72 (s, 6H), 3.57 (c, J = 7.1 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H), 2.78 (t, J = 6.8 Hz, 2H), 2.67 (t, J = 7.1 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 157.93 (2xC), 145.02 (C), 137.13 (C), 136.55 (C), 135.86 (2xC), 129.53 (4xCH), 128.74 (2xCH), 128.64 (2xCH), 127.70 (2xCH), 127.60 (2xCH), 126.51 (CH), 113.07 (4xCH), 85.37 (C), 64.65 (CH2), 62.25 (2xCH2), 54.96 (2xCH3), 35.51 (CH2).
4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)phenethyl-4-methylbenzenesulfonate 18: yield 62%; colorless oil; 1H NMR (400 MHz, DMSO-d6) δ 7.65 (d, J = 8.3 Hz, 2H), 7.35 (d, J = 7.9 Hz, 2H), 7.30–7.15 (m, 9H), 7.06 (d, J = 8.9 Hz, 4H), 6.84 (d, J = 9.0 Hz, 4H), 4.20 (t, J = 6.5 Hz, 2H), 3.72 (s, 6H), 3.12 (t, J = 6.7 Hz, 2H), 2.85 (t, J = 6.5 Hz, 2H), 2.78 (t, J = 6.6 Hz, 2H), 2.36 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ 158.49 (2xC), 145.51 (C), 145.28 (C), 137.94 (C), 136.36 (2xC), 134.92 (C), 132.73 (C), 130.50 (2xCH), 130.04 (4xCH), 129.46 (2xCH), 129.06 (2xCH), 128.27 (2xCH), 128.13 (2xCH), 127.92 (2xCH), 127.08 (CH), 113.57 (4xCH), 85.93 (C), 71.59 (CH2), 64.92 (CH2), 54.47 (2xCH3), 36.01 (CH2), 34.43 (CH2), 21.48 (CH3).
4,4’-((4-(2-azidoethyl)phenethoxy)(phenyl)methylene)bis(methoxybenzene) 19: yield 83%; colorless oil; 1H NMR (400 MHz, DMSO-d6) δ 7.32–7.20 (m,13H), 6.83 (d, J = 8.9 Hz, 4H), 3.72 (s, 6H), 3.54 (t, J = 7.0 Hz, 2H), 3.12 (t, J = 6.7 Hz, 2H), 2.80 (m, 4H); 13C NMR (100 MHz, DMSO-d6) δ 158.0 (2xC), 145.1 (C), 137.1 (C), 136.0 (C), 135.8 (2xC), 129.5 (4xCH), 129.0 (2xCH), 128.4 (2xCH), 127.6 (4xCH), 126.4 (CH), 113.1 (4xCH), 85.2 (C), 64.6 (CH2), 55.0 (CH2), 51.5 (2xCH3), 35.5 (CH2), 33.9 (CH2).
1-(4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)phenethyl)-4-phenyl-1H-1,2,3-triazole 1: yield 66%; colorless oil; 1H NMR (400 MHz, DMSO-d6) δ 8.49 (s, 1H), 7.77 (d, J = 7.0 HZ, 2H), 7.41 (t, 2H), 7.20 (m, 14H), 6.83 (d, J = 9.0 Hz, 4H), 4.63 (t, 2H), 3.72 (s, 6H), 3.19 (t, 2H), 3.11 (t, 2H), 2.77 (t, 2H);13C NMR (100 MHz, DMSOd6) δ 157.98 (C), 146.14 (C), 145.02 (C), 137.42 (C), 135.89 (2xC), 135.32 (C), 130.80 (2xC) 129.57 (4xCH), 129.08 (2xCH), 128.85 (2xCH), 128.50 (2xCH), 127.74 (2xCH), 127.62 (CH), 126.54 (CH), 125.06 (4xCH), 121.22 (CH), 113.10 (4xCH), 85.41 (C), 64.39 (CH2), 55.00 (2xCH3), 50.65 (CH2), 35.51 (CH2), 35.19 (CH2).
2-(4-(2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethyl)phenyl)ethan-1-ol 2: yield 46%; colorless oil; 1H NMR (400 MHz, DMSO-d6) δ 8.51 (s,1H), 7.80 (d, J = 7.1 Hz, 2H), 7.44 (t, 2H), 7.32 (t, 1H), 7.13 (s, 4H), 4.63 (t, 2H), 3.56 (t, 2H), 3.33 (s, 1H), 3.18 (t,2H), 2.67 (t, 2H); 13C NMR (100 MHz, DMSO-d6) δ 146.11 (C), 137.76 (C), 134.99 (C), 130.81 (C), 128.92 (2xCH), 128.86 (2xCH), 128.44 (2xCH), 127.75 (CH), 125.05 (2xCH), 121.24 (CH), 62.09 (CH2), 50.65 (CH2), 38.60 (CH2), 35.16 (CH2); HR ESMS m/z 294.1606 [M-H]+. Calc. for C18H19N3O 294.1606
1-(4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)phenethyl)-4-(4-bromophenyl)-1H-1,2,3-triazole 3: yield 56%; colorless oil; 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s,1H), 7.72 (d, J = 8.6 Hz, 2H), 7.59 (d, J = 8.7 Hz, 2H), 7.26–7.11 (m, 13H), 6.83 (d, J = 9.0 Hz, 4H), 4.64 (t, J = 7.3 Hz, 2H), 3.72 (s, 6H), 3.19 (t, J = 7.3 Hz, 2H), 3.10 (t, J = 6.7 Hz, 2H), 2.77 (t, J = 6.7 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 157.95 (2xC), 145.05 (C), 137.43 (C), 135.86 (2xC), 135.24 (C), 131.80 (2xCH), 130.02 (C), 129.54 (4xCH), 129.09 (CH), 128.48 (CH), 127.72 (CH), 127.59 (CH), 127.00 (2xCH), 126.52 (CH), 121.60 (CH), 120.67 (C), 113.07 (8xCH), 85.37 (C), 64.35 (CH2), 59.72 (C), 54.98 (2xCH3), 50.68 (CH2), 35.49 (CH2), 35.13 (CH2); HR ESMS m/z 696.1835 [M-Na]+. Calc. for C39H36N3O3Br 696.1833.
2-(4-(2-(4-(4-bromophenyl)-1H-1,2,3-triazol-1-yl)ethyl)phenyl)ethan-1-ol 4: yield 52%; white solid; m.p. 135–140 °C; 1H NMR (400 MHz, DMSO-d6) δ 8.57 (s,1H), 7.76 (d, J = 8.5 Hz, 2H), 7.64 (d, J = 8,5 Hz, 2H), 7.12 (s, 4H), 4.63 (t, 2H), 4.57 (t, 2H) 3.56 (m, 2H), 3.17 (t, 2H), 2.67 (t, 2H); 13C NMR (100 MHz, DMSO-d6) δ 145.04 (C), 137.77 (C), 134,91 (C), 131.82 (2xCH), 130.05 (C), 128.91 (2xCH), 128.40 (2xCH), 127.01 (2xCH), 121.62 (CH), 120.67 (C), 62,07 (CH2), 50,68 (CH2), 35.10 (CH2), 30.68 (CH2); HR ESMS m/z 372.0710 [M-H]+. Calc. for C18H18N3OBr 372.0711.
1-(4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)phenethyl)-4-(3-bromophenyl)-1H-1,2,3-triazole 5: yield 70%; colorless oil; 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s,1H), 7.99 (t, J = 1.7 Hz, 1H), 7.78 (dt, J = 7.9 Hz, J = 1.3 Hz, 1H), 7.51 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.37 (t, J = 7.9 Hz, 1H), 7.26–7.09 (m, 13H), 6.84 (d, J = 8.9 Hz, 4H), 4.64 (t, J = 7.3 Hz, 2H), 3.72 (s, 6H), 3.19 (t, J = 7.3 Hz, 2H), 3.10 (t, J = 6.7 Hz, 2H), 2.77 (t, J = 6.7 Hz, 2H);13C NMR (100 MHz, DMSO-d6) δ 157.96 (2xC), 145.03 (C), 144.67 (C),137.43 (C), 135.86 (2xC), 135.22 (C), 133.13 (C), 131.10 (CH), 130.41 (CH), 129.56 (4xCH), 129.09 (CH), 128.49 (CH), 127.73 (CH), 127.60 (CH), 127.49 (CH), 126.52 (CH), 123.93 (CH), 122.24 (C), 121.99 (CH), 113.08 (8xCH), 85.38 (C), 64.37 (CH2), 54.99 (2xCH3), 50.74 (CH2), 35.50 (CH2), 35.07 (CH2); HR ESMS m/z 696.1835 [M-Na]+. Calc. for C39H36N3O3Br 696.1833.
2-(4-(2-(4-(3-bromophenyl)-1H-1,2,3-triazol-1-yl)ethyl)phenyl)ethan-1-ol 6: yield 64%; white solid; m.p. 129–131 °C; 1H NMR (400 MHz, DMSO-d6) δ 8.63 (s,1H), 7.99 (s,1H), 7.82 (d, J = 7.8 Hz, 1H), 7.51 (d, J = 8.8 Hz, 1H), 7.41 (t, 1H), 7.12 (s, 4H), 4.62 (t, 2H), 4.57 (t, 1H) 3.56 (m, 2H), 3.17 (t, 2H), 2.66 (t, 2H); 13C NMR (100 MHz, DMS = -d6) δ 144.63 (C), 137.77 (C), 134,89 (C), 133.13 (CH), 131.12 (CH), 130.41 (C), 128.91 (2xCH), 128.40 (2xCH), 127.01 (CH), 123.91 (CH), 122.21 (CH), 121.98 (C), 62,07 (CH2), 50,74 (CH2), 38.59 (CH2), 35.05 (CH2); HR ESMS m/z 372.0708 [M-H]+. Calc. for C18H18N3OBr 372.0711.
1-(4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)phenethyl)-4-(2-bromophenyl)-1H-1,2,3-triazole 7: yield 40%; colorless oil; 1H NMR (400 MHz, DMSO-d6) δ 8.49 (s,1H), 7.87 (dd, J = 7.8 Hz, J = 1.7 Hz, 1H), 7.70 (dd, J = 8.1 Hz, J = 1.1 Hz, 1H), 7.46 (dt, J = 7.6 Hz, J = 1.3 Hz, 1H), 7.30–7.20 (m, 14H), 6.83 (d, J = 9.0 Hz, 4H), 4.68 (t, J = 7.3 Hz, 2H), 3.72 (s, 6H), 3.18 (t, J = 7.2 Hz, 2H), 3.11 (t, J = 6.8 Hz, 2H), 2.77 (t, J = 6.8 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 157.95 (2xC), 145.03 (C), 143.85 (C),137.33 (C), 135.87 (2xC), 135.27 (C), 133.42 (CH), 131.38 (C), 130.32 (CH), 129.67 (CH), 129.56 (4xCH), 129.05 (CH), 128.58 (CH), 127.92 (CH), 127.73 (CH), 127.61 (CH), 126.53 (CH), 124.01 (CH), 120.58 (C), 113.09 (8xCH), 85.41 (C), 64.44 (CH2), 54.98 (2xCH3), 50.64 (CH2), 35.51 (CH2), 35.38 (CH2); HR ESMS m/z 696.1835 [M-Na]+. Calc. for C39H36N3O3Br 696.1833.
2-(4-(2-(4-(2-bromophenyl)-1H-1,2,3-triazol-1-yl)ethyl)phenyl)ethan-1-ol 8: yield 75%; white solid; m.p. 130–133 °C; 1H NMR (400 MHz, DMSO-d6) δ 8.51 (s,1H), 7.89 (d, J = 7.8 Hz, 1H), 7.72 (d, J = 8.0 Hz, 1H), 7.48 (t, 1H), 7.30 (t, 1H), 7.12 (s, 4H), 4.68 (t, 2H), 4.50 (t, 1H), 3.56 (m, 2H), 3.17 (t, 2H), 2.67 (t, 2H); 13C NMR (100 MHz, DMSO-d6) δ 143.87 (C), 137.74 (C), 134,99 (C), 133.46 (CH), 131.39 (C), 130.35 (C), 129.71 (CH), 128.94 (2xCH), 128.54 (2xCH), 127.97 (CH), 124.05 (CH), 120.59 (CH), 62.17 (CH2), 50.69 (CH2), 38.64 (CH2), 35.41 (CH2); HR ESMS m/z 372.0716 [M-H]+. Calc. for C18H18N3OBr 372.0711.
1-(4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)phenethyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole 9: yield 54%; yellow oil; 1H NMR (400 MHz, DMSO-d6) δ 8.38 (s,1H), 7.69 (d, J = 8.8 Hz, 2H), 7.29–7.09 (m,13H), 6.97 (d, J = 8.9 Hz, 2H), 6.83 (d, J = 8.9 Hz,4H), 4.61 (t, J = 7.3 Hz, 2H), 3.77 (s, 3H), 3.72 (s, 6H), 3.18 (t, J = 7.3 Hz, 2H), 3.10 (t, J = 6.7 Hz, 2H), 2.77 (t, J = 6.6 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 158.92 (C), 157.96 (2xC), 146.07 (C), 145.03 (C), 137.41 (C), 135.88 (2xC), 135.36 (C), 129.56 (6xCH), 129.09 (CH), 128.51 (CH), 127.74 (CH), 127.61 (CH), 126.40 (2xCH), 123.41 (CH), 120.28 (CH), 114.27 (2xCH), 113.10 (6xCH), 85.39 (C), 64.40 (CH2), 59.75 (C), 55.13 (CH3), 54.99 (2xCH3), 50.58 (CH2), 35.51 (CH2), 35.21 (CH2); HR ESMS m/z 648.2838 [M-Na]+. Calc. for C40H39N3O4 648.2835.
2-(4-(2-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)ethyl)phenyl)ethan-1-ol 10: yield 20%; white solid; m.p. 172–174 °C; 1H NMR (400 MHz, DMSO-d6) δ 8.40 (s, 1H), 7.72 (d, J = 8.9 Hz, 2H), 7.12 (s, 4H), 7.00 (d, J = 8.9 Hz, 2H), 4.62–4.57 (m, 3H), 3.78 (s, 3H), 3.56 (m, 2H), 3.17 (t, 2H), 2.67 (t, 2H); 13C NMR (100 MHz, DMSO-d6) δ 158.93 (C), 146.04 (C), 137.75 (C), 135.03 (C), 128.92 (2xCH), 128.43 (2xCH), 126.40 (2xCH), 123.43 (C), 120.29 (CH), 114.29 (2xCH), 62.10 (CH2), 55.13 (CH3), 50.58 (CH2), 38.60 (CH2), 35.18 (CH2); HR ESMS m/z 324.1710 [M-H]+. Calc. for C19H21N3O2 324.1712.
1-(4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)phenethyl)-4-(3-methoxyphenyl)-1H-1,2,3-triazole 11: yield 74%; colorless oil; 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s,1H), 7.38–7.07 (m, 16H), 6.9–6.82 (m, 5H), 4.63 (t, J = 7.3 Hz, 2H), 3.79 (s, 3H), 3.71 (s, 6H), 3.19 (t, J = 7.3 Hz, 2H), 3.11 (t, J = 6.7 Hz, 2H), 2.77 (t, J = 6.6 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 159.69 (C), 157.99 (2xC), 146.08 (C), 145.05 (C), 137.44 (C), 135.91 (2xC), 135.32 (C), 132.16 (C), 130.03 (CH), 129.59 (4xCH), 129.11 (2xCH), 128.53 (2xCH), 127.76 (2xCH), 127.64 (2xCH), 126.56 (CH), 121.49 (CH), 117.45 (CH), 113.53 (CH), 113.11 (4xCH), 110.30 (CH), 85.43 (C), 64.43 (CH2), 55.10 (CH3), 55.00 (2xCH3), 50.69 (CH2), 35.54 (CH2), 35.20 (CH2); HR ESMS m/z 648.2838 [M-Na]+. Calc. for C40H39N3O4 648.2835.
1-(4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy) 2-(4-(2-(4-(3-methoxyphenyl)-1H-1,2,3-triazol-1-yl)ethyl)phenyl)ethan-1-ol 12: yield 55%; white solid; m.p. 90–93 °C; 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s, 1H), 7.39–7.32 (m, 3H), 7.13 (s, 4H), 6.89 (d, J = 8.2 Hz, 1H), 4.62 (t, 2H), 4.57 (t, 1H), 3.81 (s, 3H), 3.56 (c, 2H), 3.18 (t, 2H), 2.67 (t, 2H); 13C NMR (100 MHz, DMSO-d6) δ 159.65 (C), 145.99 (C), 137.75 (C), 134.96 (C), 132.13 (C), 129.98 (CH), 128.91 (2xCH), 128.41 (2xCH), 121.47 (CH), 117.39 (CH), 113.50 (CH), 110.25 (CH), 62.07 (CH2), 55.07 (CH3), 50.64 (CH2), 38.59 (CH2), 35.13 (CH2); HR ESMS m/z 324.1716 [M-H]+. Calc. for C19H21N3O2 324.1712.
1-(4-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)phenethyl)-4-(2-methoxyphenyl)-1H-1,2,3-triazole 13: yield 51%; colorless oil; 1H NMR (400 MHz, DMSO-d6) δ 8.27 (s,1H), 8.12 (dd, J=7.7 Hz, J = 1.7 Hz, 1H), 7.32–7.01 (m,16H), 6.84 (d, J = 9 Hz, 4H), 4.64 (t, J = 7.3 Hz, 2H), 3.82 (s, 3H), 3.71 (s, 6H), 3.17 (t, J=7.3 Hz, 2H), 3.11 (t, J = 6.8 Hz, 2H), 2.78 (t, J = 6.7 Hz, 2H); 13C NMR (100 MHz, DMSOd6) δ 157.99 (2xC), 155.30 (C), 145.05 (C), 141.58 (C), 137.38 (C), 135.90 (2xC), 135.48 (C), 129.59 (4xCH), 129.08 (2xCH), 128.81 (CH), 128.60 (2xCH), 127.77 (2xCH), 127.63 (2xCH), 126.54 (2xCH), 123.85 (CH), 120.62 (CH), 119.22 (C), 113.12 (4xCH), 111.54 (CH), 85.44 (C), 64.46 (CH2), 55.37 (CH3), 55.01 (2xCH3), 50.46 (CH2), 35.54 (CH2), 30.68 (CH2); HR ESMS m/z 648.2838 [M-Na]+. Calc. for C40H39N3O4 648.2835.
2-(4-(2-(4-(2-methoxyphenyl)-1H-1,2,3-triazol-1-yl)ethyl)phenyl)ethan-1-ol 14: yield 37%; white solid; m.p. 76–80 °C; 1H NMR (400 MHz, DMSO-d6) δ 8.28 (s, 1H), 8.12 (dd, J = 7.7 Hz, 1.7Hz, 1H), 7.32 (t, 1H), 7.14 (s, 4H), 7.11 (dd, J = 8.4 Hz, 0.8 Hz, 1H), 7.04 (t, 1H), 4.64 (t, 2H), 4.59 (t, 1H), 3.88 (s, 3H), 3.57 (m, 2H), 3.17 (t, 2H), 2.68 (t, 2H); 13C NMR (100 MHz, DMS = -d6) δ 155.29 (C), 141.54 (C), 137.73 (C), 135.14 (C), 128.91 (2xCH), 128.78 (2xCH), 128.5 (CH), 126.51 (CH), 123.81 (CH), 120.60 (CH), 119.21 (C), 115.55 (CH), 62.12 (CH2), 55.41 (CH3), 50.43 (CH2), 38.62 (CH2), 35.38 (CH2); HR ESMS m/z 324.1711 [M-H]+. Calc. for C19H21N3O2 324.1712.