[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[NH:11][C:12](=O)OC(C)(C)C)=O.CO/C=[CH:22]/[C:23]([O:25][CH3:26])=[O:24].Cl.C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]2[C:4]=1[N:11]=[CH:12][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:1]2
To a solution of tert-butyl N-(2-formyl-6-methoxyphenyl)carbamate (2.85 g, 11.35 mmol) [described in Org. Lett. 2002, 4(1), 39-42] and methyl trans-3-methoxyacrylate (2.70 mL, 24.96 mmol) dissolved in 60 ml of methanol, was added slowly 40 mL of an aqueous solution of hydrochloric acid 3M. The resulting mixture was stirred under reflux for 3 hours. The reaction mixture was then cooled to room temperature and neutralised by adding Na2CO3. The aqueous solution was extracted with CH2Cl2 (4×70 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under vacuum giving 2.12 g of compound of molecular formula C12H11NO3. The crude product was used without further purification in the next stage. Aspect: orange powder.
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