反应详情

温度

150 °C

To 790 mg of sodium amide were added 20 mL of N,N-dimethylanaline and 2.74 g of 4-t-butyl pyridine at r.t. The mixture was stirred at 150° C. for 6 hours. During this period, 3 more portions of sodium amide (790 mg each) were added. The reaction was cooled down to r.t. The mixture was partitioned between EtOAc and water. Aqueous layer was extracted with EtOAc (3×). The combined organic phase was washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography with 50% EtOAc in hexanes followed by 100% EtOAc to give 1.68 g of the title compound as a solid: 1H NMR (500 MHz, CDCl3) δ1.21 (s, 9H), 4.55 (br, 2H) 6.44 (t, J=1.1 Hz, 1H), 6.62 (dd, J=5.5, 1.8 Hz, 1H), 7.94 (d, J=5.5Hz, 1H).

1. waitDuring this period
2. temperatureThe reaction was cooled down to r.t
3. customThe mixture was partitioned between EtOAc and water
4. extractionAqueous layer was extracted with EtOAc (3×)
5. washThe combined organic phase was washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography with 50% EtOAc in hexanes