[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(N(CC)CC)C.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)(Cl)Cl.O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[O:4]=[C:3]([CH:5]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]
A solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added to a cold (0°) solution of 0.015 moles of ethyl acetoacetate in 75 ml of tetrahydrofuran. After the mixture was stirred for 15 minutes, a solution of 0.060 mole of triethylamine in 15 ml of tetrahydrofuran was added dropwise over five minutes. After the mixture was stirred an additional 15 minutes, a solution of 0.015 moles of benzaldehyde in 15 ml of tetrahydrofuran was added over 10 minutes. The reaction mixture was then stirred for 20 hours, after which the title compound was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2.
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