반응 #80289

반응 방정식

sodium hydroxide

phosphorus oxychloride

N,N-dimethylformamide

benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate

N,N-dimethylformamide

→

desired compound

수율 81.5%

Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3-formyl-2-methylindol-4-carboxylate

수율 81.5%

반응 조건

후처리

1. 1
   온도under cooling with ice
2. 2
   workup.ADDITIONthe solution was dropwise added to the above mixture
3. 3
   온도under cooling with ice
4. 4
   workup.STIRRINGThe mixture was stirred for 30 minutes
5. 5
   추출for adjustment to pH9, followed by extraction with ethyl acetate
6. 6
   세척The organic layer was washed with water
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   기타The residue obtained by concentration under reduced pressure
9. 9
   기타was crystallized from isopropyl ether

실험 절차

0.46 ml of phosphorus oxychloride was dropwise added to 1.8 ml of N,N-dimethylformamide under cooling with ice, and the mixture was stirred for 30 minutes. Then, 2.3 g of benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 10 ml of N,N-dimethylformamide, and the solution was dropwise added to the above mixture under cooling with ice. The mixture was stirred for 30 minutes, and then poured into ice water. An aqueous sodium hydroxide solution was added thereto for adjustment to pH9, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2 g (yield: 81.5%) of the desired compound. mp: 148°-149° C.

출처