反应详情

A mixture of N-{3-hydroxy-4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenyl}-acetamide (1 g, 3.5 mmol) and HCl (5 mL) was heated at reflux for 1 h. The mixture was basified with Na2CO3 solution to pH 9 and then extracted with EtOAc (20 mL×3). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography (petroleum ether—EtOAc, 100:1) to obtain 2-(1-(2-methoxyethoxy)-2-methylpropan-2-yl)-5-aminophenol (C-25) (61 mg, 6%). 1HNMR (CDCl3) δ 9.11 (br s, 1 H), 6.96-6.98 (d, J=8 Hz, 1 H), 6.26-6.27 (d, J=4 Hz, 1 H), 6.17-6.19 (m, 1 H), 3.68-3.69 (m, 2 ), 3.56-3.59 (m, 4 H), 3.39 (s, 3 H), 1.37 (s, 6 H); ESI-MS 239.9 m/z (MH+).

1. temperaturewas heated
2. temperatureat reflux for 1 h
3. extractionextracted with EtOAc (20 mL×3)
4. washThe combined organic layers were washed with water and brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated to dryness
7. customThe residue was purified by column chromatography (petroleum ether—EtOAc, 100:1)