반응 #5344

반응 방정식

tetronic acid

triethylamine

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

stearolic acid

HCl

→

4-hydroxy-3-(1-oxo-9-octadecynyl)-2(5H)-furanone

수율 56.0%

용매

methanol ethyl acetate

dimethylformamide

반응 조건

후처리

1. 1
   추출extracted with three 50 mL portions of ether
2. 2
   건조The combined organic layers are dried over MgSO4
3. 3
   농축concentrated in vacuo
4. 4
   기타affording crude compound

실험 절차

To a stirring solution of 1.62 g (17.86 mmol) of tetronic acid in 50 mL of dimethylformamide is added 2.5 mL (17.86 mmol) of triethylamine and 652 mg of 4-dimethylaminopyridine at 0° C. Next, 3.71 g (19.35 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.86 mmol) of stearolic acid are added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material was obtained by flash chromatography with 10% methanol/ethyl acetate as eluant affording 3.3 g (56%) of 4-hydroxy-3-(1-oxo-9-octadecynyl)-2(5H)-furanone.

출처