2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → HCID 72948938, compound

Participants

Reaction Steps

To a solution of 3-fluoro-4-(1H-pyrrol-1-yl)aniline (0.80 g, 4.55 mmol) in CH2Cl2 (30 mL) was added trimethylaluminum (23 mL, 23 mmol, 1 M in heptane) slowly. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (785 mg, 5.0 mmol) in CH2Cl2 (10 mL). The reaction mixture was stirred at rt for 3 days, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (100 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:2) to give the title compound as a pale yellow solid (450 mg, 35%). The compound was characterized by the following spectroscopic data:

Provenance & Evidence