反应详情

A solution of 4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]-3-propylphenol (0.37 g, 1.10 mmol) in dry DMF (4 mL) was cooled in an ice bath and treated with NaH (0.13 g, 3.3 mmol, 60% oil dispersion). After 10 min, ethyl bromoacetate (0.37 mL, 3.3 mmol) was added. The ice bath was removed, and the mixture was placed in an oil bath (T=85° C.). After 18 h, the reaction mixture was cooled and concentrated in vacuo. The residue was partitioned between EtOAc (70 mL) and water (40 mL). The organic layer was dried (Na2SO4) and concentrated. The crude product was purified by radial chromatography using 5% ethyl acetate in dichloromethane to give a white solid (0.34 g, 73%). 1H NMR (400 MHz, CDCl3), δ 7.97 (dd, J=7.8, 2.4 Hz, 2H), 7.41-7.39 (m, 3H), 6.77-6.73 (m, 2H), 6.61-6.63 (m, 1H, 4.54 (s, 1H), 4.28-4.24 (m, 2H), 2.96 (t, J=6.4 Hz, 2H), 2.50 (t, J=7.1 Hz, 2H), 2.37 (s, 3H), 1.51 (q, J=7.6 Hz, 2H), 1.31-1.29 (m, 5H), 0.84 (t, J=7.0 Hz, 3H); MS (FIA) m/e 424 (M+1).

1. customThe ice bath was removed
2. customthe mixture was placed in an oil bath
3. custom(T=85° C.)
4. waitAfter 18 h
5. temperaturethe reaction mixture was cooled
6. concentrationconcentrated in vacuo
7. customThe residue was partitioned between EtOAc (70 mL) and water (40 mL)
8. dry with materialThe organic layer was dried (Na2SO4)
9. concentrationconcentrated
10. customThe crude product was purified by radial chromatography