반응 #63848

반응 방정식

n-Butylamine

triethylamine

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

ethyl chloroformate

→

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

용매

tetrahydrofuran

반응 조건

후처리

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
   농축The reaction mixture was concentrated
5. 5
   workup.ADDITIONthe concentrate was diluted with water
6. 6
   추출extracted with two portions of ethyl acetate (100 ml×2)
7. 7
   세척The combined extracts were washed with successively an aqueous sodium carbonate solution and brine
8. 8
   건조dried over magnesium sulfate
9. 9
   기타evaporated to dryness
10. 10
    세척eluting with chloroform containing 2% methanol

실험 절차

(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).

출처