Réaction #5367

Équation de réaction

tetronic acid

triethylamine

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

palmitic acid

HCl

→

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

Rendement 91.0%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionextracted three times with ethyl acetate
2. 2
   LavageThe combined organic layers are washed with brine
3. 3
   Séchagedried over MgSO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   AutreThe residue is recrystallized from pentane

Mode opératoire

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.

Source