[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])=[O:7].[C:17]1(=[O:23])[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]1.Cl>C1(C)C=CC=CC=1>[C:9]([CH:8]([CH:19]1[CH2:20][CH2:21][CH2:22][C:17](=[O:23])[CH2:18]1)[C:6]([O:5][CH2:4][CH3:3])=[O:7])(=[O:10])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1To a suspension of 60 mg (0.0025 mole) of sodium hydride in 7 ml of toluene was added 4.32 ml (0.025 mole) of ethyl benzoyl acetate. After several minutes a solution was obtained to which was added 2.41 ml (0.025 mole) of cyclohexenone. The reaction was stirred 36 hrs. at room temperature and then added to 25 ml 1 N hydrochloric acid--25 ml saturated sodium chloride--150 ml ether. The ether extract was dried over magnesium sulfate and evaporated to an oil. This crude oil was purified via column chromatography on 300 g of silica gel eluted with 50% ether--pentane to yield 4.8 g (67%) of the title compound as an oil.
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