[O:1]=[C:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=O.C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.O>[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=[C:3]([C:2](=[O:1])[CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6][CH3:7])=[O:5]
A mixture of methyl 3-oxo-5-phenylpentanoate (10 g, 48.5 mmol), 2,6-dichlorobenzaldehyde (8.486 g, 48.5 mmol), acetic acid (0.56 ml, 9.7 mmol), and piperidine (0.24 ml, 2.42 mmol) in benzene (100 ml) was refluxed with azeotropic removal of water for 3 h. After cooling down the mixture, the whole was washed with water, NaHCO3 aqueous solution, and brine. The mixture was dried over Na2SO4 and evaporation of the solvent afforded a crude viscous oil, which was used for subsequent reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers. 1H NMR (CDCl3) δ 7.56 and 7.60 (each s, total 1H), 7.20 (m, 8H), 3.59 and 3.83 (each s, total 3H), 3.14-2.83 (m, 4H),.
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