反应 #944038

反应方程式

propionaldehyde

diisopropylamine

4′-methoxy-2-bromoacetophenone

→

title compound

收率 54.7%

3-(4-Methoxybenzoyl)-2-methylpropionaldehyde

收率 54.7%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   workup.WAITthe mixture was left
2. 2
   workup.WAITthe mixture was left
3. 3
   workup.WAITto stand at room temperature overnight
4. 4
   过滤The reaction mixture was then filtered
5. 5
   workup.ADDITION55 ml of 1N aqueous hydrochloric acid were added to the filtrate
6. 6
   其他to separate it into liquid phases
7. 7
   其他The aqueous layer was separated
8. 8
   萃取extracted twice with ethyl acetate
9. 9
   洗涤washed with water and with a saturated aqueous solution of sodium chloride, in that order
10. 10
    干燥The resulting solution was then dried over anhydrous magnesium sulfate
11. 11
    浓缩concentrated by evaporation under reduced pressure
12. 12
    其他The residue thus obtained
13. 13
    洗涤eluted with a 2:1 by volume mixture of hexane and ethyl acetate

实验过程

4.36 g (75 mmol) of propionaldehyde were added dropwise under a stream of nitrogen to a solution of 6.46 g (50 mmol) of diisopropylamine, 39 g of molecular sieves 4 Å and 10 mg of 2,6-di-t-butyl-4-methylphenol in 50 ml of tetrahydrofuran, and the mixture was left to stand for 3 hours. At the end of this time, 5.73 g (25 mmol) of 4′-methoxy-2-bromoacetophenone were added to the mixture, and the mixture was left to stand at room temperature overnight. The reaction mixture was then filtered, and 55 ml of 1N aqueous hydrochloric acid were added to the filtrate to separate it into liquid phases. The aqueous layer was separated and extracted twice with ethyl acetate. The organic extracts were combined and washed with water and with a saturated aqueous solution of sodium chloride, in that order. The resulting solution was then dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 2:1 by volume mixture of hexane and ethyl acetate, to give 2.82 g (yield 26%) of the title compound as a pale yellow oily substance.

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