反应详情

To a solution of 3-(5-(4-carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol (1.0 g, 2.48 mmol) and 2-bromoethyl methacrylate (0.5 g, 2.59 mmol) in DMF (20.0 ml) was added K2CO3 (4.0 g, 28.94 mmol) at room temperature under stirring. The reaction was carried out at room temperature for 23.5 h. Water (100.0 ml) was added. Brown solid product was obtained by filtration. The crude product was purified by silica gel column chromatography using dichloromethane/ethyl acetate (9.7:0.3) as eluent. After removal of solvent, white glass-like solid product was dissolved in acetone. The acetone solution was slowly dropped into methanol (60.0 ml) under stirring. After addition of acetone solution, water (30.0 ml) was added into this solution. White solid product was obtained and collected by filtration. After vacuum dry, the product as white solid in 0.98 g (76.6%) was obtained. 1H NMR (400 MHz, CDCl3, δ): 8.37 (d, J=8.0 Hz, 2H), 8.14 (dd, J1=8.0 Hz, J2=0.8 Hz, 2 Hz), 7.78-7.72 (m, 4H), 7.50-7.41 (m, 5H), 7.31 (m, 2H), 7.12 (dd, J1=8.0 Hz, J2=2.4 Hz, 1H), 6.16 (d, J=0.4 Hz, 1H, C═C—H), 5.59 (t, J=0.8 Hz, 1H, C═C—H), 4.55 (t, J=4.8 Hz, 2H, OCH2), 4.33 (t, J=4.8 Hz, 2H, OCH2), 1.96 (s, 3H, CH3). 13C NMR (100 MHz, CDCl3, δ): 167.28, 164.57, 164.06, 140.94, 140.22, 135.89, 130.40, 128.59, 127.21, 126.21, 124.97, 123.78, 122.34, 120.58, 120.47, 119.79, 118.74, 112.47, 109.87, 66.22, 62.86, 18.30. [M]+ calcd for C32H25N3O4, 515.2. found 515.2. Anal. Calcd for C32H25N3O4: C, 74.55; H, 4.89; N, 8.15. Found: C, 74.29; H, 4.79; N, 8.13.

1. customBrown solid product was obtained by filtration
2. customThe crude product was purified by silica gel column chromatography
3. customAfter removal of solvent, white glass-like solid product
4. dissolutionwas dissolved in acetone
5. additionThe acetone solution was slowly dropped into methanol (60.0 ml)
6. stirringunder stirring
7. additionAfter addition of acetone solution, water (30.0 ml)
8. additionwas added into this solution
9. customWhite solid product was obtained
10. filtrationcollected by filtration
11. customAfter vacuum dry