反应详情

A solution of 4-benzyloxy-2-propylphenol (0.50 g, 1.94 mmol) in dry DMF (7 mL) was cooled in an ice bath and treated with NaH (0.15 g, 3.8 mmol, 60% oil dispersion). The ice bath was removed, ethyl bromoacetate (0.43 mL, 3.9 mmol) was added, 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 diluted with EtOAc, washed with brine (2×), dried (Na2SO4), and concentrated. The crude product was purified by radial chromatography using 10% ethyl acetate in hexanes to give a tan solid (0.62 g, 97%). 1H NMR (400 MHz, CDCl3) δ 7.44-7.31 (m, 5H), 6.82 (d, J=2.9 Hz, 1H), 6.72 (dd, J=8.8, 2.9 Hz, 1H), 6.66 (d, J=8.8 Hz, 1H), 5.00 (s, 2H), 4.57 (s, 2H), 4.25 (q, J=7.0 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H), 1.64 (q, J=7.5 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H); MS (FIA) m/e 329 (M+1).

1. customThe ice bath was removed
2. customthe mixture was placed in an oil bath
3. custom(T=85° C.)
4. temperaturethe reaction mixture was cooled
5. concentrationconcentrated in vacuo
6. additionThe residue was diluted with EtOAc
7. washwashed with brine (2×)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated
10. customThe crude product was purified by radial chromatography