反应详情

温度

60 °C

To a stirred solution of methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (5.0 g, 19.5 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (3.47 g, 19.5 mmol) and AIBN (160 mg, 5 mol %) at room temperature. The reaction mixture was heated at 60° C. for 3 h, cooled to room temperature, and filtered through a small pad of CELITE®. The filtrate was concentrated in vacuo to give light yellow colored residue which was dissolved in EtOAc and washed with 10% NaHCO3 solution. The organic layer was dried over Na2SO4 and concentrated to give crude compound. The crude material was purified by flash chromatography (gradient from 20 to 30% EtOAc/hexanes), to provide the title compound (2.85 g, 43%). 1H NMR (CDCl3) δ 7.76 (s, 1H), 5.30 (s, 2H), 3.90 (s, 3H), 3.55 (t, J=8.0 Hz, 2H), 0.92 (t, J=8.0 Hz, 2H), 0.01 (s, 9H); MS(ESI+) m/z 335.0 (M+H)+.

1. temperaturecooled to room temperature
2. filtrationfiltered through a small pad of CELITE®
3. concentrationThe filtrate was concentrated in vacuo
4. customto give light yellow colored residue which
5. washwashed with 10% NaHCO3 solution
6. dry with materialThe organic layer was dried over Na2SO4
7. concentrationconcentrated
8. customto give crude compound
9. customThe crude material was purified by flash chromatography (gradient from 20 to 30% EtOAc/hexanes)