2,4-Dichlorobenzaldehyde → 1-(3-Chloro-2-fluoro-phenyl)-5-(2,4-dichloro-phenyl)-3-hydroxy-4-isobutyryl-1,5-dihydro-pyrrol-2-one

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Reaction Conditions

Reaction Steps

A mixture of 3-chloro-2-fluoro-aniline (428 mg, 2.94 mmol) and 2,4-dichloro-benzaldehyde (515 mg, 2.94 mmol) was heated to 110° C., stirred for 4 h, allowed to cool to rt, and diluted with toluene (5 mL). A solution of the sodium salt of 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (615 mg, 2.94 mmol) in dioxane (5 mL) and acetic acid (0.17 mL) were added. The resulting mixture was refluxed for 15 h, allowed to cool to rt and diluted with EtOAc and water. The aqueous layer was separated and extracted with EtOAc. 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→95:5) to provide 660 mg of the title compound. tR: 1.40 min (LC-MS 1); ESI-MS: 443.8 [M+H]+ (LC-MS 1).

Provenance & Evidence