反应详情

温度

0 °C

LDA (2 M) (10.5 mL, 21.22 mmol) was added drop-wise to a solution of 3-picoline (2.17 g, 23.34 mmol) in THF (60 mL) at −78° C. The mixture was stirred for 30 min and then 1,11-dibromoundecane (10 g, 31.83 mmol) was added in one portion. The resulting mixture was warmed to 0° C. and stirred for 4 hrs. Fifty percent saturated NH4Cl was added to the reaction mixture. The aqueous phase was extracted with ethylacetate (2×40 mL), and the combined organic liquors were washed with 50% saturated brine (3×40 mL) and saturated brine (40 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was purified by column chromatography (hexanes:ethylacetate 4:1) to afford 4.47 g 12-(pyridin-3-yl)-1-bromododecane. Yield: 59%.

1. stirringstirred for 4 hrs
2. extractionThe aqueous phase was extracted with ethylacetate (2×40 mL)
3. washthe combined organic liquors were washed with 50% saturated brine (3×40 mL) and saturated brine (40 mL)
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by column chromatography (hexanes:ethylacetate 4:1)