反应详情

温度

55 °C

5-Benzyloxy-2-but-1-enylphenol (0.70 g, 2.75 mmol) was dissolved in anhydrous DMF (12 mL), followed by the addition of ethyl bromoisobutyrate (1.62 mL, 11.0 mmol), and cesium carbonate (3.58 g, 11.0 mmol). The mixture was then heated for 18 h (55° C.). The reaction mixture was then cooled and concentrated in vacuo. The crude residue was partitioned between EtOAc (70 mL) and water (40 mL). The organic layer was washed with brine, dried (Na2SO4), and removed in vacuo. The crude residue was purified using radial chromatography, eluting with 5% EtOAc/Hex to give 0.77 g (76%) of a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.41-7.28 (m, 6H), 6.65-6.59 (m, 2H), 6.40 (d, J=2.4 Hz, 1H), 6.14-6.07 (m, 1H), 4.99 (s, 2H), 4.22 (q, J=7.2 Hz, 2H), 2.22 (quintet, J=7.6 Hz, 2H), 1.56 (s, 6H), 1.26 (t, J=7.1 Hz, 3H), 1.08 (t, J=7.6 Hz, 3H), MS (ES) m/e 369 (M+1).

1. temperatureThe reaction mixture was then cooled
2. concentrationconcentrated in vacuo
3. customThe crude residue was partitioned between EtOAc (70 mL) and water (40 mL)
4. washThe organic layer was washed with brine
5. dry with materialdried (Na2SO4)
6. customremoved in vacuo
7. customThe crude residue was purified
8. washeluting with 5% EtOAc/Hex