3-Chloro-2-fluoroaniline → 1-(3-Chloro-2-fluoro-phenyl)-5-(4-chloro-2-methyl-phenyl)-3-hydroxy-4-isobutyryl-1,5-dihydro-pyrrol-2-one

Participants

Reaction Steps

A mixture of 3-chloro-2-fluoro-aniline (0.70 g, 4.8 mmol), 4-chloro-2-methyl-benzaldehyde (0.74 g, 4.8 mmol) and the sodium salt of 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (1.0 g, 4.8 mmol) in acetic acid (6 mL) was refluxed for 3 h. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 1:0→9:1), followed by crystallization from EtOAc/hexane, to provide 426 mg of the title compound. tR: 5.47 min (HPLC 1); ESI-MS: 422 [M+H]+ (LC-MS 1).

Provenance & Evidence