Реакция #330766

Уравнение реакции

NH4Cl

LDA

3-picoline

THF

1,10-dibromodecane

THF

→

title compound

Выход 75.0%

1,12-bis-(pyridin-3-yl)-dodecane

Выход 75.0%

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred for 4 hrs
2. 2
   ЭкстракцияThe aqueous phase was extracted with ethylacetate (2×40 mL)
3. 3
   Промывкаthe combined organic liquors were washed with 50% saturated brine (3×40 mL) and saturated brine (40 mL)
4. 4
   Сушкаdried over anhydrous Na2SO4
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe crude product was purified by column chromatography (hexanes:ethylacetate 2:1 to 1:1)

Методика

LDA (2M) (20.40 mL, 40.80 mmol) was added drop-wise to a solution of 3-picoline (3.80 g, 40.80 mmol) in THF (60 mL) at −78° C. The mixture was stirred for 30 min and then 1,10-dibromodecane (6.43 g, 16.32 mmol) in THF (10 mL) was added drop-wise. The resulting mixture was warmed to room temperature 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 2:1 to 1:1) to afford 3.98 g of the title compound. Yield: 75%. 1H NMR (300 MHz, CDCl3) δ 1.17-1.40 (m, 16H), 1.53-1.68 (m, 4H), 2.60 (t, J=7.5 Hz, 4H), 7.20 (dd, J=7.8, 1.8 Hz, 2H), 7.48 (dt, J=7.8, 1.8 Hz, 2H), 8.43 (d, J=5.1 Hz, 2H), 8.44 (s, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 29.4, 29.7, 29.8, 29.9, 31.4, 33.3, 123.3, 135.8, 138.4, 147.2, 150.0 ppm.

Источник