反应 #1121794

反应方程式

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

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

trifluoroacetic acid

→

4-(4-bromo-pyridin-2-yl)-4-oxo-butyraldehyde

4-(4-Bromo-pyridin-2-yl)-4-oxo-butyraldehyde

溶剂

CH2Cl2

反应条件

后处理

1. 1
   浓缩The reaction is concentrated
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (150 mL)
3. 3
   洗涤washed with water 3 times
4. 4
   干燥dried over Na2SO4
5. 5
   其他the solvent evaporated
6. 6
   其他The residue is purified by flash column chromatography (30% EtOAc in hexanes)

实验过程

To a solution of 1-(4-bromo-pyridin-2-yl)-4,4-dimethoxy-butan-1-one (2) (crude from Step 2, 11 g, 38.2 mmol) in 100 of CH2Cl2 at room temperature is added trifluoroacetic acid (10.9 g, 95.4 mmol) and the reaction mixture is stirred overnight. The reaction is concentrated, the residue dissolved in ethyl acetate (150 mL) and washed with water 3 times. The organic layers are combined, dried over Na2SO4 and the solvent evaporated. The residue is purified by flash column chromatography (30% EtOAc in hexanes) to give 4-(4-bromo-pyridin-2-yl)-4-oxo-butyraldehyde (3) as an yellow oil. (4.16 g, 45%): MS ES+244.04.

来源