[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([N:9]([CH3:11])[CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[CH2:14]([O:16][CH:17]([O:36][CH2:37][CH3:38])[C:18]1[CH:35]=[CH:34][C:21](/[CH:22]=[N:23]/[C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH2:26][O:27][C:28]3=[O:33])=[CH:20][CH:19]=1)[CH3:15].[CH3:39][O-].[Na+].[C:42](OCC)(=[O:45])CC>>[CH2:14]([O:16][CH:17]([O:36][CH2:37][CH3:38])[C:18]1[CH:19]=[CH:20][C:21]([CH:22]2[CH:1]([C:3]3[CH:13]=[CH:12][C:6]([C:7](=[O:8])[N:9]([CH3:11])[CH3:10])=[CH:5][CH:4]=3)[C:42](=[O:45])[C:25]3[C:29]([C:28]([O:27][CH2:26][CH3:39])=[O:33])=[CH:30][CH:31]=[CH:32][C:24]=3[NH:23]2)=[CH:34][CH:35]=1)[CH3:15]To a mixture of 4-formyl-N,N-dimethylbenzamide (960 mg, 5.42 mmol), (E)-4-(4-(diethoxymethyl)benzylideneamino) isobenzofuran-1(3H)-one (1.84 g, 5.42 mmol) and sodium methoxide (499 mg, 21.7 mmol) was added to ethyl propionate (30 mL) and the mixture was stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with EtOAc (100 mL×4) and concentrated. This gave the crude product (250 mg). LC-MS (ESI) m/z: 545 (M+1)+.
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