反应详情

温度

100 °C

To a mixture of 4-chloro-3-nitrobenzaldehyde 57 (5.099 g, 27 mmol), cesium carbonate (9.48 g, 29 mmol), and methyl piperidine-4-carboxylate (4 mL, 27 mmol) was added DMSO (27 mL). The reaction mixture was heated to 100° C. for 30 min and diluted with EtOAc. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 30% to 50% EtOAc in hexanes) gave methyl 1-(4-formyl-2-nitrophenyl)piperidine-4-carboxylate 58 (3.45 g, 43% yield) as a yellow oil. Mass spectrum: calculated for C14H16N2O5 292.1. found 293.1 (M++1).

1. washThe organic phase was washed with water (2×), brine (1×)
2. dry with materialdried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customPurification by flash column chromatography on silica gel (eluted with 30% to 50% EtOAc in hexanes)