Реакция #348632

Уравнение реакции

triethylamine

3-pyridylmethanol

1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid

thionyl chloride

→

1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid-3 -pyridylmethyl ester

Выход 79.7%

Растворители

tetrahydrofuran

water

tetrahydrofuran

benzene

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling
2. 2
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
3. 3
   Другоеto leave a residue
4. 4
   Температураunder cooling
5. 5
   Другоеthe solvent was removed by distillation under reduced pressure
6. 6
   Другоеto leave a residue
7. 7
   Другоеan oily substance was obtained
8. 8
   Экстракцияextracted with chloroform
9. 9
   Промывкаthe adsorbate was eluted with ether
10. 10
    Другоеto give crystals
11. 11
    ДругоеRecrystallization of the crystals from a mixed solvent of ethyl acetate ester and ether

Методика

A mixture of 3.0 g of 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid and 3.0 g of thionyl chloride was refluxed in 70 ml of benzene for 3 hours. After cooling, the solvent was distilled off under reduced pressure to leave a residue. The residue was dissolved in 20 ml of tetrahydrofuran. This solution was added to a solution of 1.0 g of 3-pyridylmethanol in 70 ml of tetrahydrofuran under cooling. To this mixture was carefully added 0.95 g of triethylamine and stirring was continued for 2 hours at room temperature. After the reaction was complete, the solvent was removed by distillation under reduced pressure to leave a residue. After addition of water to the residue, an oily substance was obtained and extracted with chloroform. The extract was applied on a column of silica gel and the adsorbate was eluted with ether to give crystals. Recrystallization of the crystals from a mixed solvent of ethyl acetate ester and ether yielded 3.0 g of 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid-3 -pyridylmethyl ester, melting at 116°-118° C. Analysis--Calculated for C25H21ClN2O4 : C, 66.89; H, 4.72; N, 6.24. Found: C, 67.06; H, 4.68; N, 6.11.

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