[Cl:1][CH2:2][C:3](=O)[CH:4]=[CH:5][Cl:6].[C:8]([O:15][CH3:16])(=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11].N1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl.O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:13][O:12][C:10](=[O:11])[C:9]([C:8]([O:15][CH3:16])=[O:14])=[C:3]([CH2:2][Cl:1])/[CH:4]=[CH:5]/[Cl:6]Titanium tetrachloride (0.1 dm3, 0.9 mole) in carbon tetrachloride (0.1 dm3) was added to stirred tetrahydrofuran (0.25 dm3) at 0° over 5 minutes. To the yellow solution a premix of 1,4-dichloro-3-buten-2-one (0.0556 kg, 0.4 mole) and dimethyl malonate (0.0528 kg, 0.4 mole) in tetrahydrofuran (0.2 dm3) was added dropwise over 10 minutes maintaining the temperature at 0°. A solution of pyridine (0.13 dm3, 1.6 moles) in tetrahydrofuran (0.1 dm3) was added to the above brown mixture dropwise over 30 minutes at 0° and the resultant mixture stirred at ambient temperature for three hours and then treated with water (1 dm3). The mixture was separated, the aqueous phase re-extracted with dichloromethane (2×0.25 dm3) and the combined organic extract washed with brine (2×0.1 dm3) and then dried over magnesium sulphate (0.10 kg). Filtration and evaporation of the filtrate under reduced pressure gave a red oil which crystallised on standing. Yield 0.064 kg (63.3%), m.p. 56°.
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