反应详情

To a solution of tert-butyl 2-formyl-6-(trifluoromethyl)phenylcarbamate (0.40 g, 1.40 mmol) in 10 mL of benzene was added diethyl malonate (0.21 mL, 1.40 mmol), piperidine (0.015 mL, 0.15 mmol) and benzoic acid (17 mg, 0.14 mmol). The resulting mixture was allowed to stir at 80° C. for 6 h while water was collected in a Dean-Stark trap. The reaction was allowed to cool and was diluted with EtOAc. The organics were washed with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 0.58 g (96%) of the title compound as an oil which solidified on standing. 1H NMR (CDCl3): δ 7.89 (s, 1H), 7.70-7.63 (m, 2H), 7.35 (t, 1H, J=7.7 Hz), 6.30 (broad s, 1H), 4.26-4.17 (m, 4H), 1.46 (s, 9H), 1.36-1.26 (m, 6H). LRMS (ESI): 432.32 (M+H)+.

1. customwas collected in a Dean-Stark trap
2. temperatureto cool
3. additionwas diluted with EtOAc
4. washThe organics were washed with 1N HCl
5. dry with materialdried (MgSO4)
6. filtrationfiltered through a pad of silica gel
7. concentrationconcentrated in vacuo