Реакция #5358

Уравнение реакции

HCl

thiotetronic acid

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

linoleic acid

→

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

Выход 30.0%

Растворители

dimethylformamide

triethylamine

Условия реакции

Обработка

1. 1
   Экстракцияextracted three times with diethyl ether
2. 2
   ПромывкаThe combined organic layers are washed with brine
3. 3
   Сушкаdried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe residue is recrystallized from pentane at -78° C.
7. 7
   Другоеto give a solid which
8. 8
   Температураupon warming to room temperature

Методика

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.

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