Pyridine → Ethyl 3-(4-methylphenyl)-2-propenoate

Participants

Reaction Steps

A solution of 3 (11.6 g, 96.9 mmol) and 4 (16.7 g, 126 mmol) in piperidine (958 μL, 9.69 mmol) and pyridine (39.2 mL, 485 mmol) was refluxed for 8 h under argon. The reaction mixture was cooled to room temperature and the reaction was quenched with 2 N HCl (˜250 mL). The reaction mixture was extracted with ether. The extracts were washed with water, base (NaHCO3), and water. The organic solution was dried (Na2SO4), concentrated, and chromatographed (silica, CH2Cl2) to give a colorless oil (14.6 g, 79%): 1H NMR δ 1.33 (t, J=7.2 Hz, 3H), 2.37 (s, 3H), 4.26 (q, J=7.2 Hz, 2H), 6.39 (d, J=15.8 Hz, 1H), 7.18 (d, J=8.2 Hz, 2H), 7.42 (d, J=8.2 Hz, 2H), 7.66 (d, J=15.8 Hz, 1H); 13C NMR δ 14.5 21.6, 60.6, 117.4, 128.2, 129.8, 131.9, 140.8, 144.8, 167.4; Anal. Calcd for C12H14O2: C, 75.76; H, 7.42. Found: C, 75.76; H, 7.44.

Provenance & Evidence