Water → HCID 67442780, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-{[1-(3,5-difluoro-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (4.27 g, 14.8 mmol) and ytterbium(III) triflate hydrate (0.92 g, 1.48 mmol) in dry tetrahydrofuran (50 mL) at 25° C. was added isobutyraldehyde (1.34 mL, 14.8 mmol) and water (0.27 mL, 14.8 mmol) dropwise. The reaction mixture was stirred at 25° C. for 5 h. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-(3,5-difluoro-phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (5.34 g, 100%) as a light yellow oil: LC/MS m/e calcd for C20H21F2NO3 M+: 361.4, observed: 344.2.

Provenance & Evidence