反应详情

In an atmosphere of argon, activated zinc powder (4.88 g, 0.07 g atom) was suspended in anhydrous tetrahydrofuran (THF) (25.0 ml) to which was subsequently added dropwise several drops of ethyl bromoacetate while heating under reflux. When color of the reaction solution became green, 3-cyanopyridine (1.59 g, 15.0 mmol) was added to the solution, ethyl bromoacetate (6.0 ml, 51.4 mmol) was added dropwise thereto spending 50 minutes and then the mixture was heated under reflux for 15 minutes. After cooling, the reaction solution was diluted with THF, mixed with 50% potassium carbonate aqueous solution (15.0 ml) and then stirred for 30 minutes. After standing, the organic layer was collected and extracted three times with THF in the same manner and then the thus obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:1-4:1) to obtain the title compound (2.26 g, 72.3%) as pale yellow oil.

1. temperaturewhile heating
2. temperatureunder reflux
3. additionwas added dropwise
4. temperaturethe mixture was heated
5. temperatureunder reflux for 15 minutes
6. temperatureAfter cooling
7. customthe organic layer was collected
8. extractionextracted three times with THF in the same manner
9. dry with materialthe thus obtained organic layer was dried over anhydrous magnesium sulfate
10. customThe solvent was evaporated under reduced pressure
11. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:1-4:1)