8-Methoxyquinoline → 8-Methoxy-2-(2-methoxyphenyl)quinoline

Participants

Reaction Steps

A solution of 8-methoxyquinoline (5.54 g, 34.8 mmol, 1.0 eq) in 55 ml diethyl ether was slowly dropped (within about 30 min) into a solution of o-lithioanisole (4.37 g, 38.4 mmol, 1.1 eq) in 55 ml diethyl ether (each 55 mL). A yellow green fluorescing solution was formed. At the conclusion of the addition, stirring was continued at room temperature for a further 2 hours, after which no more educt could be detected by thin layer chromatography. During the reaction, the color of the reaction mixture changed from fluorescent yellow to green to green-brown. The reaction mixture was worked up by adding it to ice and subsequent extraction with diethyl ether (3×40 ml). The combined organic phases (yellow) were dried over MgSO4 and the solvent was removed in a rotary evaporator. The residue was dissolved in 200 ml dichloromethane and stirred with ca. 40 equivalents of activated manganese dioxide (Merck) until the thin layer chromatographic control (ethyl acetate/hexane=4/6) showed that all of the crude product had reacted. The manganese dioxide was filtered off and the solvent removed in the rotary evaporator. The product was dried under vacuum.

Provenance & Evidence