Trimethylsilyl cyanide → HCID 53308978, compound

HRID 2389883Notes

Reaction equation

HRID 2389883 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH2:7]([C:9]1[C:20]([CH2:21]O)=[C:12]2[C:13]3[CH2:19][CH2:18][O:17][C:14]=3[CH:15]=[CH:16][N:11]2[N:10]=1)[CH3:8]>ClCCl.C(=O)([O-])O.[Na+]>[CH2:7]([C:9]1[C:20]([CH2:21][C:5]#[N:6])=[C:12]2[C:13]3[CH2:19][CH2:18][O:17][C:14]=3[CH:15]=[CH:16][N:11]2[N:10]=1)[CH3:8]

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 53308851(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol

Product 1

HCID 53308978HCID 53308978, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

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%).

Workup

  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→30/70)

Sources & evidence

ORD record
ord-b44f98967a7641c987d5480ad216ed0a
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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