Potassium Cyanide → HCID 18177464, compound

HRID 394683Notes

Reaction equation

HRID 394683 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH:7]([CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:6]2.[C-:25]#[N:26].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH:7]([CH2:13][C:25]#[N:26])[CH2:6]2

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 57176004HCID 57176004, compound

Product 1

HCID 18177464HCID 18177464, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.6 g (4.56 mmol) of the tosylate obtained in Step B are dissolved in 25 ml of anhydrous N,N-dimethylformamide; 0.724 g (11.5 mmol) of potassium cyanide is then added to the solution. After 4 hours of reflux under argon, the solvent is evaporated in vacuo; the residue is then taken up in a saturated solution of sodium hydrogen carbonate. The aqueous phase is then extracted with dichloromethane. The organic phases, dried over magnesium sulphate and then filtered, are concentrated under reduced pressure. The title nitrile is obtained pure in the form of an oil which crystallises slowly after chromatography on silica gel (eluant: AcOEt/PE: 25/75).

Workup

  1. temperatureAfter 4 hours of reflux under argon
  2. customthe solvent is evaporated in vacuo
  3. extractionThe aqueous phase is then extracted with dichloromethane
  4. dry with materialThe organic phases, dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-80e5fae366fc422c96b948722490bd7d
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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