تفاعل #5358

معادلة التفاعل

HCl

thiotetronic acid

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

linoleic acid

→

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

المردود 30.0%

المذيبات

dimethylformamide

triethylamine

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted three times with diethyl ether
2. 2
   غسيلThe combined organic layers are washed with brine
3. 3
   تجفيفdried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue is recrystallized from pentane at -78° C.
7. 7
   أخرىto give a solid which
8. 8
   درجة الحرارةupon warming to room temperature

الإجراء التجريبي

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.

المصدر