Reaktion #453502

Reaktionsgleichung

hydrochloric acid

3-(4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

aluminum chloride

propionyl chloride

→

desired product

Ausbeute 56.3%

3-(4-chloro-2-propionyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

Ausbeute 56.3%

Lösungsmittel

nitromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder cooling with ice
2. 2
   workup.ADDITIONAfter completion of the dropwise addition
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed sequentially with water
6. 6
   Trocknena saturated s odium chloride aqueous solution and then dried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   SonstigeThen, the obtained residue was purified by silica gel column chromatography

Vorschrift

1.3 g (1.4 mmol) of 3-(4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 1.9 g (1.4 mmol) of aluminum chloride, were dissolved in 20 ml of nitromethane, and 0.5 g (1.4 mmol) of propionyl chloride was dropwise added thereto under cooling with ice. After completion of the dropwise addition, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction solution was poured into a mixture of dilute hydrochloric acid and ice and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated s odium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.33 g (yield: 56%) of the desired product as a yellow glassy substance. Refractive index: unmeasurable, 1H-NMR (solvent, CDCl3): 1.20(3H,m), 2.91(2H,q), 3.56(3H,s), 6.38(1H,s), 7.28(1H,d), 7.58(1H,s)ppm

Quelle