Reaktion #5358

Reaktionsgleichung

HCl

thiotetronic acid

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

linoleic acid

→

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

Ausbeute 30.0%

Lösungsmittel

dimethylformamide

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted three times with diethyl ether
2. 2
   WaschenThe combined organic layers are washed with brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue is recrystallized from pentane at -78° C.
7. 7
   Sonstigeto give a solid which
8. 8
   Temperaturupon warming to room temperature

Vorschrift

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.

Quelle