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Trans-cinnamaldehyde (1.84 ml, 14.8 mmol), five drops of piperidine and five drops of acetic acid were added to a solution of 4-pyridyl acetone (2.0 g, 14.8 mmol) in toluene (25 ml). The mixture was heated to reflux for 48 hours with a Dean-Stark trap to remove water. The mixture was concentrated to give a black oil. The oil was purified by silica gel chromatography (eluted with 1:1 hexane/ethyl acetate). The desired fractions were collected, combined and concentrated to give 6-phenyl-3-(4-pyridinyl)hexa-3,5-dien-2-one (628 mg). The ketone was further purified by an additional column chromatography on silica gel (eluting with hexane-ethyl acetate-methylene chloride-methanol (1:1:2:0.12)) (380 mg, 27.3%): Anal. Calc'd for C17H15NO 0.4 H2O: C, 79.91; H, 5.84; N, 5.48. Found: C, 79.72; H, 5.91; N, 5.25. MS (M+H+) : 250.

1. temperatureThe mixture was heated
2. temperatureto reflux for 48 hours with a Dean-Stark trap
3. customto remove water
4. concentrationThe mixture was concentrated
5. customto give a black oil
6. customThe oil was purified by silica gel chromatography (eluted with 1:1 hexane/ethyl acetate)
7. customThe desired fractions were collected
8. concentrationconcentrated