1-Piperidinecarboxaldehyde → HCID 71743951, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-chloro-4-fluoro-2-(4-fluorophenyl)-3-iodobenzofuran (2.0 g, 5.12 mmol) in THF (15 ml) under a N2 atmosphere in a 50 ml two necked RB flask cooled to 78° C. was added n-butyllithium (0.328 g, 5.12 mmol) slowly, and the mixture stirred at the same temperature for 1 hour. 1-Piperidinecarboxaldehyde (5.79 g, 51.2 mmol) was then added and the mixture was maintained stirring at the same temperature for 3 hours. The reaction mixture was quenched with 1N HCl and extracted with diethyl ether (3×25 ml). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give the titled compound (1.2 g, 74%). 1H NMR (400 MHz, CDCl3): δ 10.39 (d, J=2.4 Hz, 1H), 8.18-8.14 (m, 2H), 7.44-7.40 (m, 1H), 7.33 (d, J=9.2, 1H), 7.27-7.23 (m, 2H).

Provenance & Evidence