Reaktion #5367

Reaktionsgleichung

tetronic acid

triethylamine

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

palmitic acid

HCl

→

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

Ausbeute 91.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted three times with ethyl acetate
2. 2
   WaschenThe combined organic layers are washed with brine
3. 3
   Trocknendried over MgSO4
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue is recrystallized from pentane

Vorschrift

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.

Quelle