반응 #5343

반응 방정식

tetronic acid

triethylamine

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

palmitoleic acid

HCl

→

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

수율 36.0%

용매

methanol ethyl acetate

dimethylformamide

반응 조건

후처리

1. 1
   추출extracted with four 100 mL portions of ethyl acetate
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 1.07 g (10.72 mmol) of tetronic acid in 30 mL of dimethylformamide is added 1.64 mL (11.97 mmol) of triethylamine and 428 mg of 4-dimethylaminopyridine at 0° C. Next, 2.44 g (12.77 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.0 g (11.79 mmol) of palmitoleic acid are added and the reaction is stirred for 3 days at room temperature. The reaction is acidified with 1.0N HCl and extracted with four 100 mL portions of ethyl acetate. 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 1.3 g (36%) of 4-hydroxy-3-((Z)-1-oxo-9-hexadecenyl)-2(5H)-furanone.

출처