反应详情

A solution of methyl 3-(allyl(4-fluorophenyl)amino)-3-oxopropanoate (10 g, 39.7 mmol) in acetic acid (50 mL) was added into a suspension of manganese (III) acetate dihydrate (21 g, 79.7 mmol) and copper (II) acetate monohydrate (7.9 g, 39.7 mmol) in acetic acid (200 mL). The reaction was allowed to stir for 3 days at room temperature. The reaction was quenched with 10% aqueous sodium bisulfite solution (100 mL). The reaction mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3, brine, dried with Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (50% EtOAc in hexane) to afford the product (1.2 g, 12% yield) as a brown power. LRMS (APCI pos) m/e 250.1 (M+1). 1H NMR: (CDCl3, 400 MHz) δ 7.49-7.54 (m, 2H), 7.02-7.07 (m, 2H), 4.02-4.07 (m, 1H), 3.83 (s, 3H), 3.70 (d, 1H), 2.45-2.53 (m, 1H), 2.02-2.09 (m, 1H), 1.29-1.33 (m, 1H).

1. customThe reaction was quenched with 10% aqueous sodium bisulfite solution (100 mL)
2. additionThe reaction mixture was diluted with EtOAc
3. washwashed with saturated aqueous NaHCO3, brine
4. dry with materialdried with Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by flash column chromatography (50% EtOAc in hexane)