Reaktion #2477065

Reaktionsgleichung

trimethylsilyl cyanide

(2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol

→

title compound

Ausbeute 59.2%

(2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)acetonitrile

Ausbeute 59.2%

Lösungsmittel

dichloromethane

dichloromethane

sodium hydrogen carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   TrocknenThe extract was dried over anhydrous sodium sulfate
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   Sonstigethe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70)

Vorschrift

To a solution of boron trifluoride diethyl ether complex (836 μL, 6.60 mmol) and trimethylsilyl cyanide (1.17 mL, 8.77 mmol) in dichloromethane (5 mL) was added a solution of (2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol (480 mg, 2.20 mmol) in dichloromethane (10 mL) under ice-cooling and an argon atmosphere, and the mixture was stirred at room temperature for 30 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70) to give the title compound (296 mg, yield 59%).

Quelle