反应详情

温度

-78 °C

Diethylmethylphosphonate (302.8 mg, 2 mmol) was dissolved in anhydrous THF (2.5 ml), the mixture was cooled to −78° C. under argon, n-butyllithium (2.11 mmol, 846 μl of a 2.5 M solution in hexane) was added dropwise with stirring. After addition was complete, stirring was continued for 20 minutes, after which ethyl 4-(4-quinolyl)piperazine-1-carboxylate (284 mg, 1 mmol) dissolved in 0.5 μl THF was added dropwise. The mixture was allowed to reach room temperature overnight with continued stirring. Glacial acetic acid (0.25 ml) and water (2 ml) was added, after which the mixture was basified with 0.1 NaOH and extracted with diethylether (2×). The organic phases were combined, washed with 5% sodium bicarbonate and water. The aqueous phases were back-extracted with diethylether after basification with 0.1 N NaOH and the combined organic phases dried over magnesium sulfate and the solvent was removed under reduced pressure to yield 271 mg (0.693 mmol, 69%). MS (ESI): m/z=392.1 [M+1]+.

1. additionAfter addition
2. stirringstirring
3. additionwas added dropwise
4. waitto reach room temperature overnight with continued stirring
5. extractionextracted with diethylether (2×)
6. washwashed with 5% sodium bicarbonate and water
7. extractionThe aqueous phases were back-extracted with diethylether after basification with 0.1 N NaOH
8. dry with materialthe combined organic phases dried over magnesium sulfate
9. customthe solvent was removed under reduced pressure
10. customto yield 271 mg (0.693 mmol, 69%)