Reacción #5367

Ecuación de reacción

tetronic acid

triethylamine

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

palmitic acid

HCl

→

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

Rendimiento 91.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted three times with ethyl acetate
2. 2
   LavadoThe combined organic layers are washed with brine
3. 3
   Secadodried over MgSO4
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroThe residue is recrystallized from pentane

Procedimiento

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.

Fuente