2-Methylpyridine → 1-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methoxyphenyl]-2-pyridin-2-yl-ethanol

Participants

Reaction Conditions

Reaction Steps

2-Picoline (40 μl) was dissolved in tetrahydrofuran (2 ml), and the solution was cooled to −78° C. under an argon atmosphere. n-Butyllithium (1.56 M hexane solution) (260 μl) was added to the cooled solution, and the mixture was stirred for 2 hr. A solution of 2-(6,7-dimethoxy-quinolin-4-yloxy)-5-methoxy-benzaldehyde (100 mg) in tetrahydrofuran (2 ml) was then added to the reaction solution, and the mixture was stirred at −78° C. for one hr. A saturated ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (37 mg, yield 29%).

Provenance & Evidence