Ethanol → (2E)-N-Benzo[b]furan-5-yl-3-[4-(tert-butyl)phenyl]prop-2-enamide

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Reaction Conditions

Reaction Steps

Methyl 2-(2-formyl-4-nitrophenoxy)acetate. To a round-bottomed flask was added a suspension of 2-hydroxy-5-nitrobenzaldehyde (10 g, 60 mmol, Aldrich) in anhydrous EtOH (180 mL). The suspension was treated with KOH (4.4 g, 66 mmol) and heated under N2 with magnetic stirring in a 65° C. oil bath for 45 min. The reaction mixture was allowed to cool to 25° C. and concentrated in vacuo. Anhydrous DMF (180 mL) was added, and the reaction flask was cooled in an ice bath and charged with methyl bromoacetate (10 mL, 110 mL, Aldrich). The reaction mixture was stirred for 3.5 h at 25° C., then the solvent was removed in vacuo. Water (200 mL) was added, and the mixture was extracted with EtOAc (3×50 mL). The combined organic extract was washed with 1 M H3PO4, satd NaHCO3, and satd NaCl. After drying over MgSO4, the organic layer was filtered and concentrated in vacuo. The residue was recrystallized from CH2Cl2 and hexane to afford the title product as a pale yellow solid. MS (ESI, pos. ion) m/z: 240 (M+1).

Provenance & Evidence