Dimethylcarbamoyl Chloride → 4-(Tert-butyl-dimethylsilyloxyethyl)-2-cyanopyridine

HRID 2420992Notes

Reaction equation

HRID 2420992 reaction equation
[O:1]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N+:14]([O-])=[CH:13][CH:12]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].C[Si]([C:22]#[N:23])(C)C.CN(C)C(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[O:1]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:22]#[N:23])[CH:12]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 197577894-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1-oxo-1lambda~5~-pyridine

Product 1

HCID 223217094-(Tert-butyl-dimethylsilyloxyethyl)-2-cyanopyridineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(tert-Butyldimethylsiloxy)ethyl]pyridine-N-oxide (12.5 g, 49.3 mmol) was dissolved in dichloromethane (100 mL), then trimethylsilyl cyanide (5.31 g, 53.5 mmol) was added thereto at room temperature, and dimethylcarbamoyl chloride (5.76 g, 53.5 mmol) was added thereto over 30 minutes. Then, the mixture was stirred for 24 hours. After completion of the reaction was confirmed by thin-layer chromatography, a 10% aqueous potassium carbonate solution (150 mL) was added to the mixture, and the mixture was further stirred for 10 minutes. The reaction mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give 4-[2-(tert-butyldimethylsiloxy)ethyl]pyridine-2-carbonitrile (12.5 g, yield 97%).

Workup

  1. stirringthe mixture was further stirred for 10 minutes
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-383c76ab88fd44a2abaf691f9c4d88fd
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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