Reacción #5343

Ecuación de reacción

tetronic acid

triethylamine

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

palmitoleic acid

HCl

→

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

Rendimiento 36.0%

Disolventes

methanol ethyl acetate

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with four 100 mL portions of ethyl acetate
2. 2
   SecadoThe combined organic layers are dried over MgSO4
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   Otroaffording crude compound

Procedimiento

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.

Fuente