反応 #80289

反応方程式

sodium hydroxide

phosphorus oxychloride

N,N-dimethylformamide

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

N,N-dimethylformamide

→

desired compound

収率 81.5%

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

収率 81.5%

反応条件

後処理

1. 1
   温度under cooling with ice
2. 2
   workup.ADDITIONthe solution was dropwise added to the above mixture
3. 3
   温度under cooling with ice
4. 4
   workup.STIRRINGThe mixture was stirred for 30 minutes
5. 5
   抽出for adjustment to pH9, followed by extraction with ethyl acetate
6. 6
   洗浄The organic layer was washed with water
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   その他The residue obtained by concentration under reduced pressure
9. 9
   その他was crystallized from isopropyl ether

実験手順

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.

出典