反应详情

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.

1. customthe whole was reacted for 3 hours at room temperature
2. customthe solvent was removed by distillation under reduced pressure
3. customThe residue thus obtained
4. extractionextracted with ethyl ether
5. customThe ether layer separated
6. washwas washed with water
7. customdried
8. customThe ether was removed by distillation
9. customto yield crystals
10. customRecrystallization of the crystals from petroleum ether