反应详情

温度

60 °C

The compound 8 was prepared according to the general procedure described for the compound 6 above employing 4 (0.15 g, 0.47 mmol, 1 eq) and thiophenol (0.051 g, 0.05 mL, 0.47 mmol, 1 eq), Cs2CO3 (0.38 g, 1.2 mmol, 2.6 eq), CuI (0.044 g, 0.23 mmol, 0.49 eq) and L1 (0.042 g, 0.23 mmol, 0.49 eq) heating the reaction mixture at 60° C. for 10 h to give crude product, which was purified by silica gel column chromatography (100% hexane) to give compound 8, as white crystals (0.12 g, 90%). [When a mixture of Z and E-4 (1:9) was used as the starting material under same conditions at a temperature above 100° C. afforded a mixture of Z and E-8 (1:9). They were distinguished from each other by their coupling constants. Jcis=5.7 Hz while Jtrans=12 Hz (1H-NMR data of these mixtures are found below).] The characterization data below is that of 8 obtained from the reaction 4 with thiophenol: mp 92-96° C. 1H NMR (300 MHz, CD2Cl2): 7.66-7.54 (m, 4H, HAr), 7.48-7.40 (m, 2H, HAr), 7.37-7.28 (br s, 6H, HAr), 7.20-7.09 (m, 3H, HAr), 6.09-6.10 (d, 2H CH═CH, J=12.0 Hz) ppm; 13C NMR (300 MHz, CDCl3): 155.9, 150.6, 140.3, 137.5, 137.1, 128.9, 128.8, 128.5, 127.2, 127.0, 126.9, 125.7, 117.4, 102.1; IR (cm−1): 3054, 2985, 1659, 1624, 1599, 1515, 1485, 1265, 1233, 1185, 1174, 1112, 1086, 1025, 1007, 924, 839, 739, 407; HRMS (ESI) Calculated for C20H16OS [M+H]+ 305.1000. Found 305.0998. Elemental analysis Calculated for C20H16OS0.11 H2O: C, 78.40; H, 5.34. found: C, 78.40; H, 5.29.

1. customThe compound 8 was prepared
2. customto give crude product, which
3. customwas purified by silica gel column chromatography (100% hexane)