[O-:1][CH2:2][CH3:3].[Na+].[C:5]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:6][C:7]([O-:9])=O.I[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1>C(O)C.O>[CH2:2]([O:1][C:7]([CH:6]([CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1)[C:5]([O:11][CH2:12][CH3:13])=[O:10])=[O:9])[CH3:3]To a solution of sodium ethoxide (90%, 6.79 g) in ethanol (250 ml) was dropwise added ethyl malonate (12.0 g) with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 30 min and ethyl 4-(3-iodopropoxy)benzoate (25.0 g) was dropwise added with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1) to yield the entitled compound (13.0 g) as an oil.
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