Benzoic Acid → HCID 20147155, compound

Participants

Reaction Steps

A mixture of 3-(1-tridecynyl)pyridine-4-carboxaldehyde (7.13 g, 25 mmole, from Example 1), diethyl malonate (4.12 g), benzoic acid (0.145 g) and piperidine (0.18 ml) in benzene (45 ml) was refluxed under conditions of water removal for 24 hours. After cooling, ether was added and the solution was washed with dilute sodium bicarbonate solution and dried. Evaporation and distillation of excess diethyl malonate under reduced pressure afforded an oil which on silica gel chromatography gave 4.90 g (46%) of the title compound as a pale yellow oil, bp0.1 250° C. (Kugelrohr), νmax (film) 2930, 2850, 2220, 1730, 1640, 1250, 1215 cm-1 ; δ(CDCl3) 0.83 (3H, distorted t, terminal CH3), 1.12-1.65 (24H, m, ester CH3 +alkylene envelope), 2.43 (2H, t, J 6 Hz, CH2C≡C), 4.22 (2H, q, J 7 Hz, ester CH2), 4.30 (2H, q, J 7 Hz, ester CH2), 7.25 (1H, d, J 5 Hz, C-5H), 7.99 (1H, s, CH=C), 8.42 (1H, d, J 5 Hz, C-6H), 8.63 (1H, s, C-2H).

Provenance & Evidence