CN(C)[CH:3]=[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](=[O:7])[CH3:6].[C:15](OCC)(=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].[O-]CC.[Na+].[Na].Cl>C(O)C.O>[O:7]=[C:5]1[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][O:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6]1A solution of 4-dimethylamino-3-phenyl-3-buten-2-one (30.3 g) and diethyl oxalate (43.5 ml) in ethanol (75 ml) was added to a stirred solution of sodium ethoxide prepared by dissolving sodium (5.5 g) in ethanol (150 ml). The stirred mixture was heated under reflux for 1 hour, cooled to 20°-25° C. and acidified by addition of 5 N hydrochloric acid (150 ml). The mixture was stirred for a further hour, then cooled to 5° C., and diluted with water (300 ml). The solid title product was recrystallised from ethanol-water (mp 110°-112° C.).
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