Reaktion #80294

Reaktionsgleichung

benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylate

sodium hydride

benzoyl chloride

→

desired compound

Ausbeute 92.0%

Benzyl-1-benzoyl-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylate

Ausbeute 92.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGat room temperature, and the mixture was stirred for 4 hours
2. 2
   EinengenAfter concentration under reduced pressure
3. 3
   workup.ADDITIONthe mixture was poured into ice water
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with water
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   SonstigeThe residue obtained by concentration under reduced pressure
8. 8
   Sonstigewas crystallized from isopropyl ether

Vorschrift

1.5 g of benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylate was dissolved in 50 ml of tetrahydrofuran, and 0.176 g of 60% sodium hydride was added thereto. The mixture was stirred at room temperature for 30 minutes. Then, 0.51 g of benzoyl chloride was dropwise added thereto at room temperature, and the mixture was stirred for 4 hours. After concentration under reduced pressure, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 1.67 g (yield: 92%) of the desired compound. mp: 128°-132.5° C.

Quelle