反应详情

A solution of bis-(3-pyridyl)methane in 150 mL of THF was cooled to −30 C. LDA (1.5 M solution in cyclohexane, 29.4 mL) was added dropwise to give a dark red solution containing some red solid matter. The mixture was then stirred at 0 C for 10 min. A solution of 3-(bromomethyl)-2-chloropyridine in 50 mL of THF was added dropwise over 25 min, and the reaction was stirred at 0 C for 2 h, after which the reaction was quenched by adding saturated aqueous NH4Cl. The mixture was partitioned between saturated aqueous sodium bicarbonate and CH2Cl2. The aqueous solution was extracted with CH2Cl2 (3×), and the combined organic solutions were dried (Na2SO4) and concentrated. Flash chromatography gave 9.1 g of 2-chloro-3-(2,2-dipyridin-3-ylethyl)pyridine as a red, viscous liquid.

1. customto give a dark red solution
2. additioncontaining some red solid matter
3. stirringthe reaction was stirred at 0 C for 2 h
4. customafter which the reaction was quenched
5. additionby adding saturated aqueous NH4Cl
6. customThe mixture was partitioned between saturated aqueous sodium bicarbonate and CH2Cl2
7. extractionThe aqueous solution was extracted with CH2Cl2 (3×)
8. dry with materialthe combined organic solutions were dried (Na2SO4)
9. concentrationconcentrated