반응 #5367

반응 방정식

tetronic acid

triethylamine

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

palmitic acid

HCl

→

4-hydroxy-3-[1-oxohexadecyl]-2(5H)-furanone

수율 91.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   추출extracted three times with ethyl acetate
2. 2
   세척The combined organic layers are washed with brine
3. 3
   건조dried over MgSO4
4. 4
   농축concentrated in vacuo
5. 5
   기타The residue is recrystallized from pentane

실험 절차

To a stirring solution of 650 mg (6.5 mmol) of tetronic acid in 20 mL of dimethylformamide is added 1.0 mL (7.17 mmol) of triethylamine and 230 mg (1.88 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.50 g (7.81 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.0 g (7.81 mmol) of palmitic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ethyl acetate. The combined organic layers are washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is recrystallized from pentane to give 2.0 g (91%) of 4-hydroxy-3-[1-oxohexadecyl]-2(5H)-furanone, mp 81°-83° C.

출처