Реакция #348633

Уравнение реакции

hydrochloric acid

sodium hydride

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

chloromethylethyl ether

→

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

Выход 71.7%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеthe whole was reacted for 3 hours at room temperature
2. 2
   Другоеthe solvent was removed by distillation under reduced pressure
3. 3
   ДругоеThe residue thus obtained
4. 4
   Экстракцияextracted with ethyl ether
5. 5
   ДругоеThe ether layer separated
6. 6
   Промывкаwas washed with water
7. 7
   Другоеdried
8. 8
   ДругоеThe ether was removed by distillation
9. 9
   Другоеto yield crystals
10. 10
    ДругоеRecrystallization of the crystals from petroleum ether

Методика

To a mixture of 3.6 g of 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid and 50 ml of dry tetrahydrofuran was added 0.5 g of 50% sodium hydride and the mixture was stirred for 30 minutes. To this mixture was further added 2.5 g of chloromethylethyl ether and the whole was reacted for 3 hours at room temperature. After the reaction was complete, the solvent was removed by distillation under reduced pressure. The residue thus obtained was neutralized with diluted hydrochloric acid, and then extracted with ethyl ether. The ether layer separated was washed with water and dried. The ether was removed by distillation to yield crystals. Recrystallization of the crystals from petroleum ether yielded 3.0 g of 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid-ethoxymethyl ester as colorless prisms, melting at 60°-61° C. Analysis--Calculated for C22H22ClNO5 : C, 63.48; H, 5.17; N, 3.42. Found: C, 63.53; H, 5.33; N, 3.37.

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