反应 #1121793

反应方程式

bromopropionaldehyde dimethyl acetal

( 1 )

4-Bromo-pyridine-2-carboxylic acid methoxy-methyl-amide

→

1-(4-Bromo-pyridin-2-yl)-4,4-dimethoxy-butan-1-one

溶剂

THF

water

dry ice

THF

反应条件

后处理

1. 1
   干燥dried round bottom flask at −70° C. (acetone-dry ice bath)
2. 2
   workup.ADDITIONis slowly added the Grignard reagent
3. 3
   温度maintaining internal temperature around −68° C. to −70° C
4. 4
   其他removed
5. 5
   workup.ADDITIONThe mixture is poured into a separatory funnel
6. 6
   萃取the mixture is extracted 3 times with ethyl acetate (150 mL)
7. 7
   干燥dried over Na2SO4
8. 8
   其他the solvent evaporated
9. 9
   其他leaving a thick yellow oil (11 g, 100% crude yield, MS ES+258.02)

实验过程

To a solution of (1) (8.86 g, 36.2 mmole) in 250 mL of anhydrous THF in a 3-neck flamed dried round bottom flask at −70° C. (acetone-dry ice bath) is slowly added the Grignard reagent prepared from bromopropionaldehyde dimethyl acetal (16.5 g, 90.4 mmol) and Mg turnings (4.39 g, 181 mmol) in anhydrous THF (250 mL), maintaining internal temperature around −68° C. to −70° C. After stirring at −70° C. for 2 hours, the reaction mixture is diluted with 200 mL of water with the dry ice bath removed. The mixture is poured into a separatory funnel, and the mixture is extracted 3 times with ethyl acetate (150 mL). The organic layers are combined and dried over Na2SO4 and the solvent evaporated leaving a thick yellow oil (11 g, 100% crude yield, MS ES+258.02).

来源