反応 #6294

反応方程式

sodium chloride

4-(N-2-acetoxyethyl-N-ethylamino)benzaldehyde

1,3-dioxolan-2-ylmethyltributylphosphonium bromide

Potassium t-butoxide

→

cinnamaldehyde

4-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde

溶媒

dimethylformamide

dimethylformamide

HCl

water

反応条件

後処理

1. 1
   温度heating
2. 2
   温度After cooling to room temperature
3. 3
   乾燥The combined organics are dried over 4A sieves
4. 4
   ろ過filtered through cotton
5. 5
   その他evaporated
6. 6
   その他The crude reaction product
7. 7
   抽出After neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether
8. 8
   乾燥the combined organics are dried over 4A sieves
9. 9
   ろ過filtered through cotton
10. 10
    その他evaporated

実験手順

To a solution of 235.3 g (1 mole) of 4-(N-2-acetoxyethyl-N-ethylamino)benzaldehyde in dimethylformamide is added 738.7 g (2.0 moles) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide, and the mixture is heated at 90° C. Potassium t-butoxide (224.4 g, 2.0 moles) is added, and heating is continued at 90° C. for 16 hours. After cooling to room temperature, the solution is poured into a seven-fold excess of water, the aqueous mixture is saturated with sodium chloride, The combined organics are dried over 4A sieves, filtered through cotton, and evaporated. The crude reaction product is dissolved in 3M HCl, and the reaction is stirred at room temperature for 16 hours. After neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether, and the combined organics are dried over 4A sieves, filtered through cotton, and evaporated to yield the cinnamaldehyde as an oil. The product is purified by flash chromatography (silica gel, 1:1 hexane:ethyl acetate).

出典