Benzene → HCID 68900235, compound

Participants

Reaction Steps

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)+.

Provenance & Evidence