反应详情

温度

45 °C

To a cold (0° C.) solution of 4-chloro-2-picoline (10 g, 78.4 mmol) and ethyl 4-methoxybenzoate (14.1 g, 78.4 mmol) in tetrahydrofuran (100 mL) was added lithium bis(trimethylsilyl)amide (157 mL, 1.0 M in tetrahydrofuran, 157 mmol) dropwise via a pressure equalizing funnel over half an hour. Upon complete addition, the ice bath was removed and the resulting solution was heated at 45° C. for 15 hours. The mixture was cooled to room temperature, and the solution was concentrated. Methanol was added to quench the reaction, resulting in the formation of a yellow precipitate. The precipitate was collected by filtration and dried to give the product as a mixture of enol and ketone tautomers. MS m/z 262 (M+1).

1. customover half an hour
2. additionUpon complete addition
3. customthe ice bath was removed
4. temperatureThe mixture was cooled to room temperature
5. concentrationthe solution was concentrated
6. additionMethanol was added
7. customto quench
8. customthe reaction
9. customresulting in the formation of a yellow precipitate
10. filtrationThe precipitate was collected by filtration
11. customdried
12. customto give the product