Реакция #2856

Уравнение реакции

3-thiophene-2-yl-acrylic acid

triethylamine

tributylamine

sodium azide

ethyl chloroformate

→

title compound

Выход 49.7%

5H-Thieno[3,2-c]pyridin-4-one

Выход 49.7%

Растворители

acetone

diphenyl ether

H2O

—

hexanes

H2O

Условия реакции

Обработка

1. 1
   ФильтрацияA white precipitate forms which is collected by filtration
2. 2
   СушкаThe resulting solid is dried over P2O5 under vacuum
3. 3
   workup.WAITAfter 2 h
4. 4
   Температураthe solution is cooled to ambient temperatures
5. 5
   Температураis cooled to 0° C
6. 6
   ФильтрацияThe resulting solid is collected by filtration
7. 7
   Промывкаthe solid is washed with hexanes

Методика

To a solution of 3-thiophene-2-yl-acrylic acid (7.39 g, 47.9 mmol) in 200 mL of acetone is added triethylamine (4.9 g, 47.9 mmol). The resulting solution is cooled to 0° C. and ethyl chloroformate (5.7 g, 52.8 mmol) is added dropwise. After 2 h, sodium azide (4.67 g, 71.9 mmol) in 25 mL of H2O is then added. The solution is stirred for 1.5 h at 0° C. After this time, the solution is poured into 300 mL of H2O. A white precipitate forms which is collected by filtration. The resulting solid is dried over P2O5 under vacuum. The solid is suspended in 20 mL of diphenyl ether. This solution is added dropwise to a solution of tributylamine (6.9 g, 37.4 mmol) in 200 ml of diphenyl ether at 190° C. After 2 h, the solution is cooled to ambient temperatures. The solution is diluted with 1000 mL of hexanes and is cooled to 0° C. The resulting solid is collected by filtration and the solid is washed with hexanes. The title compound (3.6 g, 23.8 mmol) is obtained as a white solid.

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