Alpha-Methylstyrene → HCID 70497572, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-amino-benzoic acid methyl ester (0.825 g, 5 mmol) and 3-chloro-4-fluoro-benzaldehyde (869 mg, 5.5 mmol) in acetonitrile (50 mL) were added isopropenyl-benzene (2.36 g, 20 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (465 mg, 0.75 mmol). The resulting mixture was stirred at 90° C. for 16 h in sealed tube. The mixture was diluted with ethyl acetate (50 mL) and washed with water (30 mL×2) and brine (30 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether) to afford 2-(3-chloro-4-fluoro-phenyl)-4-methyl-4-phenyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (850 mg, 40%) as a light yellow solid: MS (ESI) M+1=424.2.

Provenance & Evidence