反应详情

To a stirring solution of 1-[3-(ethyloxy)-4-nitrophenyl]-4-piperidinol (4.00 g, 15.0 mmol) in DCM (150 mL) was sequentially added solid NaHCO3 (6.31 g, 75.1 mmol), Dess-Martin Periodane (7.65 g, 18.0 mmol) and H2O (0.27 mL, 15.0 mmol). The reaction was then vigorously stirred at rt for 1 h. The reaction was quenched with equal volumes of saturated sodium thiosulfate (aq) and saturated NaHCO3 (aq) and allowed to stir for an additional 0.5 h. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were then dried, filtered and concentrated in vacuo. The residue was purified by flash chromatography to afford 1-[3-(ethyloxy)-4-nitrophenyl]-4-piperidinone (2.15 g, 54%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.91 (d, J=9.3 Hz, 1H), 6.61 (dd, J=9.4, 2.6 Hz, 1H), 6.53 (d, J=2.5 Hz, 1H), 4.21 (q, J=7.0 Hz, 2H), 3.81 (t, J=6.1 Hz, 4H), 2.46-2.53 (m, 4H), 1.36 (t, J=7.0 Hz, 3H).

1. customThe reaction was quenched with equal volumes of saturated sodium thiosulfate (aq) and saturated NaHCO3 (aq)
2. stirringto stir for an additional 0.5 h
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with DCM
5. customThe combined organic layers were then dried
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash chromatography