反应详情

温度

100 °C

To a solution of 4-bromomethyl-3-nitrobenzoic acid methyl ester (1.64 g, 6.0 mmol) in DMF (15 mL) was added triphenylphosphine (1.57 g, 6.0 mmol) and the mixture was heated at 100° C. for 30 min. To this solution was added a solution of 3-(3,5-dichloro-4-formylphenyl)-propionic acid tert-butyl ester (1.50 g, 4.95 mmol) (from Example 6-25) in DMF (5 mL) in one portion, followed by pulverized potassium carbonate (1.37 g, 9.9 mmol) and the mixture was heated at 100° C. for 18 h. The reaction mixture was partitioned between ethyl acetate and water, washed with brine, dried with MgSO4, filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate/heptane to obtain 4-{(E)-2-[4-(2-tert-butoxycarbonylethyl)-2,6-dichlorophenyl]-vinyl}-3-nitrobenzoic acid methyl ester as a yellow solid. MS (m/z) 497.1 (M+18); 1H NMR (DMSO-d6, 400 MHz) δ 8.49 (d, J=1.64 Hz, 1H), 8.28 (dd. J=8.15, 1.58 Hz, 1H), 8.14 (d, J=8.21 Hz, 1H), 7.47 (s, 2H), 7.47 (d, J=16.7 Hz, 1H), 7.33 (d, J=16.4 Hz, 1H), 3.93 (s, 3H), 2.83 (t, J=7.33 Hz, 2H), 2.58 (t, J=7.33 Hz, 2H), 1.37 (s, 9H).

1. temperaturethe mixture was heated at 100° C. for 18 h
2. customThe reaction mixture was partitioned between ethyl acetate and water
3. washwashed with brine
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude residue was purified by flash chromatography on silica gel
8. washeluting with a gradient of 0-50% ethyl acetate/heptane