반응 #5347

반응 방정식

tetronic acid

triethylamine

HCl

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

6-(4-heptylphenoxy)heptanoic acid

→

3-[6-(4-heptylphenoxy)-1-oxohexyl]-4-hydroxy-2(5H)-furanone

수율 50.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   추출extracted with three 200 mL portions of ether
2. 2
   건조The combined organic layers are dried over MgSO4
3. 3
   농축concentrated in vacuo

실험 절차

To a stirring solution of 1.1 g (10.98 mmol) of tetronic acid in 25 mL of dimethylformamide is added 1.53 mL (10.98 mmol) of triethylamine and 400 mg of 4-dimethylaminopyridine at 0° C. Next, 2.28 g (11.98 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.38 g (10.98 mmol) of 6-(4-heptylphenoxy)heptanoic acid are added and the reaction mixture is stirred for 3 days at room temperature. The reaction mixture is acidified with 1.0N HCl and extracted with three 200 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo. Trituration of the crude product in ethyl acetate/hexane affords 2.1 g (50%) of 3-[6-(4-heptylphenoxy)-1-oxohexyl]-4-hydroxy-2(5H)-furanone.

출처