反应详情

温度

90 °C

A solution of 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine (2.95 g, 10 mmol) and phenylsuccinic anhydride (1.94 g, 11 mmol) in toluene was refluxed for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. A mixture of the residue and sodium acetate (0.86 g, 10.5 mmol) in acetic anhydride (60 ml) was stirred at 90° C. for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and removed under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate−4/1) to obtain 2.27 g (yield 50%) of the title compound. mp. 130–131° C. low polarity product, 1H-NMR (CDCl3) δ: 1.00 (3H, s)=1.52 (3H, s), 1.64 (3H, s), 2.02 (3H, s), 2.16 (3H, s), 2.30 (3H, s), 3.00 (1H, dd, J=4.7, 18.5 Hz), 3.36 (1H, dd, J=9.5, 18.5 Hz), 4.15–4.25 (2H, m), 6.85 (2H, br), 7.06 (2H, brd, J=6.6 Hz), 7.30–7.47 (5H, m).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionThe residue was diluted with water
3. extractionextracted with ethyl acetate
4. washThe extract was washed with saturated aqueous sodium chloride
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was removed under reduced pressure
7. concentrationThe reaction mixture was concentrated under reduced pressure
8. additionThe residue was diluted with water
9. extractionextracted with ethyl acetate
10. washThe extract was washed with saturated aqueous sodium chloride
11. dry with materialdried over anhydrous sodium sulfate
12. customremoved under reduced pressure
13. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate−4/1)