Trimethylsilyl cyanide → 8,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylacetonitrile

HRID 2389882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2389882
C[Si]([C:5]#[N:6])(C)C.[C:7]1([CH2:19]O)[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][CH2:18][C:12]=3[C:11]=12>ClCCl.C(=O)([O-])O.[Na+]>[C:7]1([CH2:19][C:5]#[N:6])[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][CH2:18][C:12]=3[C:11]=12

Komponenten

5

Edukt 2

HCID 82115Trimethylsilyl cyanideHCID 591793818,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylmethanol

Produkt 1

HCID 591793778,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylacetonitrileAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of boron trifluoride diethyl ether complex (1.26 mL, 9.94 mmol) and trimethylsilyl cyanide (1.77 mL, 13.3 mmol) in dichloromethane (13 mL) was added a solution of 8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylmethanol (630 mg, 3.31 mmol) in dichloromethane (39 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→40/60) to give the title compound (274 mg, yield 42%).

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Quellen und Nachweise

ORD-Eintrag
ord-ce2c374aff41485a856250562bfee595
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273761B2

Notizen zur Reaktion

Wird geladen…