반응 #5358

반응 방정식

HCl

thiotetronic acid

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

linoleic acid

→

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

수율 30.0%

용매

dimethylformamide

triethylamine

반응 조건

후처리

1. 1
   추출extracted three times with diethyl ether
2. 2
   세척The combined organic layers are washed with brine
3. 3
   건조dried over Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue is recrystallized from pentane at -78° C.
7. 7
   기타to give a solid which
8. 8
   온도upon warming to room temperature

실험 절차

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.

출처