反応 #63848

反応方程式

n-Butylamine

triethylamine

(E,E)-4-Ethyl-2,4-hexadienoic acid

ethyl chloroformate

→

(E,E)-N-n-butyl-4-ethyl-2,4-hexadienamide

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGat -20° C. with stirring
2. 2
   workup.STIRRINGThe resulting mixture was stirred at the same temperature for 60 minutes
3. 3
   workup.STIRRINGThe resulting mixture was stirred at the same temperature for 60 minutes
4. 4
   濃縮The reaction mixture was concentrated
5. 5
   workup.ADDITIONthe concentrate was diluted with water
6. 6
   抽出extracted with two portions of ethyl acetate (100 ml×2)
7. 7
   洗浄The combined extracts were washed with successively an aqueous sodium carbonate solution and brine
8. 8
   乾燥dried over magnesium sulfate
9. 9
   その他evaporated to dryness
10. 10
    洗浄eluting with chloroform containing 2% methanol

実験手順

(E,E)-4-Ethyl-2,4-hexadienoic acid (5 g) was dissolved in tetrahydrofuran (300 ml) and triethylamine (5 ml) was added to the solution. The mixture was stirred at room temperature for 30 minutes and then ethyl chloroformate (3.4 ml) was added dropwise thereto at -20° C. with stirring. The resulting mixture was stirred at the same temperature for 60 minutes. n-Butylamine (3.6 ml) was added to the reaction mixture at -20° C. The resulting mixture was stirred at the same temperature for 60 minutes. The reaction mixture was concentrated and the concentrate was diluted with water, and then extracted with two portions of ethyl acetate (100 ml×2). The combined extracts were washed with successively an aqueous sodium carbonate solution and brine, dried over magnesium sulfate and then evaporated to dryness to given an oil (6.5 g) which was subjected to column chromatography on silicagel, eluting with chloroform containing 2% methanol, to give (E,E)-N-n-butyl-4-ethyl-2,4-hexadienamide (5.8 g).

出典