反应详情

温度

-10 °C

To a solution of 12.9 g (145 mmol) of 2-N,N-dimethylaminoethanol in 100 mL of hexanes, 116 mL (290 mmol) of 2.5 M nBuLi in hexanes was added dropwise with vigorous stirring at −10° C. This mixture was slowly warmed to 0° C., stirred for 30 min, and then 7.54 g (48.6 mmol) of 2-phenylpyridine was added at −10° C. The resulting mixture was stirred for 2 hr at 0° C. and then added dropwise to a solution of 43.2 g (179 mmol) of 16 in 725 mL of THF at −10° C. This mixture was slowly warmed to room temperature, stirred for 12 hr, and then 20 mL of water was added. The organic solvent was evaporated using a rotary evaporator. 17 was isolated from the residue by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-ethyl acetate=5:1, vol.). The obtained product was additionally washed with 30 mL of diethyl ether and then dried in vacuum. Yield 11.0 g (62%) of white solid.

1. temperatureThis mixture was slowly warmed to 0° C.
2. stirringstirred for 30 min
3. stirringThe resulting mixture was stirred for 2 hr at 0° C.
4. temperatureThis mixture was slowly warmed to room temperature
5. stirringstirred for 12 hr
6. customThe organic solvent was evaporated
7. customa rotary evaporator
8. custom17 was isolated from the residue by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-ethyl acetate=5:1, vol.)
9. washThe obtained product was additionally washed with 30 mL of diethyl ether
10. customdried in vacuum