反应详情

温度

0 °C

N-ethyldiisopropylamine (147 μL, 0.84 mmol, 3 equiv) was added to a solution of 38 (100 mg, 0.28 mmol, 1 equiv) in CH2Cl2 (5 mL) at 0° C. After 10 min, methyl 3-chloro-3-oxopropionate (60 μL, 0.56 mmol, 2 equiv) was added and the reaction was stirred at 0° C. for 3 h. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (100 mL). The organic layer was dried over MgSO4, filtered, concentrated and the residue purified by silica gel flash column chromatography (30% EtOAc:hexanes) to provide 41 (87 mg, 68%) as a yellow oil. 1HNMR (400 MHz, DMSO-d6): δ 10.00 (s, 1H), 7.68 (s, 1H), 7.56 (m, 1H), 7.33-7.17 (m, 8H), 7.06-7.03 (m, 1H), 6.53 (m, 2H), 3.86 (s, 3H), 3.61 (s, 3H), 3.37 (s, 2H), 2.17 (s, 3H). MS m/z 455.87 (M+H)+.

1. washwashed with saturated aqueous NaHCO3 (100 mL)
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customthe residue purified by silica gel flash column chromatography (30% EtOAc:hexanes)