反应详情

温度

60 °C

To a solution of (1H-benzoimidazol-2-yl)-methanol (501 mg, 3.38 mmol) and allyl bromide (0.29 mL, 3.38 mmol) in DMF (15 mL) was added N,N-diisopropylethylamine (0.71 mL, 4.06 mmol). The reaction mixture was stirred at 60° C. overnight. Then the mixture was cooled to room temperature and quenched with saturated NaHCO3 (25 mL). Then it was extracted with CH2Cl2 (3×25 mL). The combined organic layer was washed with brine (2×25 mL), dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a brown oil. Purification by flash column chromatography on silica gel using 2% CH3OH/CH2Cl2 afforded the product as a yellow oil (180 mg, 28%). 1H NMR (CDCl3) δ 4.85 (br s, 5H), 4.98 (d, 1H, J=17.1 Hz), 5.17 (d, 1H, J=10.5 Hz), 5.88-6.01 (m, 1H), 7.20-7.26 (m, 3H), 7.66 (t, 1H, J=3.9 Hz).

1. temperatureThen the mixture was cooled to room temperature
2. customquenched with saturated NaHCO3 (25 mL)
3. extractionThen it was extracted with CH2Cl2 (3×25 mL)
4. washThe combined organic layer was washed with brine (2×25 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customdried in vacuo
9. customto afford a brown oil
10. customPurification by flash column chromatography on silica gel using 2% CH3OH/CH2Cl2