Reacción #5358

Ecuación de reacción

HCl

thiotetronic acid

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

linoleic acid

→

4-hydroxy-3-[(Z,Z)-1-oxo-9,12-octadecadienyl]-2(5H)-thiophenone

Rendimiento 30.0%

Disolventes

dimethylformamide

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted three times with diethyl ether
2. 2
   LavadoThe combined organic layers are washed with brine
3. 3
   Secadodried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue is recrystallized from pentane at -78° C.
7. 7
   Otroto give a solid which
8. 8
   Temperaturaupon warming to room temperature

Procedimiento

To a stirring solution of 1.71 g (14.75 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 2.22 ML (17.2 mmol) of triethylamine and 592 mg (4.85 mmol) of 4-dimethylaminopyridine at 0° C. Next, 3.38 g (17.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4.96 g (17.7 mmol) of linoleic 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 diethyl ether. The combined organic layers are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is recrystallized from pentane at -78° C. to give a solid which melts upon warming to room temperature giving 1.67 g (30%) of 4-hydroxy-3-[(Z,Z)-1-oxo-9,12-octadecadienyl]-2(5H)-thiophenone as an oil.

Fuente