反应详情

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.

1. customA yellow green fluorescing solution was formed
2. additionAt the conclusion of the addition
3. customDuring the reaction
4. additionby adding it
5. extractionto ice and subsequent extraction with diethyl ether (3×40 ml)
6. dry with materialThe combined organic phases (yellow) were dried over MgSO4
7. customthe solvent was removed in a rotary evaporator
8. dissolutionThe residue was dissolved in 200 ml dichloromethane
9. customhad reacted
10. filtrationThe manganese dioxide was filtered off
11. customthe solvent removed in the rotary evaporator
12. customThe product was dried under vacuum