Potassium Cyanide → HCID 18177409, compound

HRID 394673Notes

Reaction equation

HRID 394673 reaction equation
I[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[C-:15]#[N:16].[K+].C(=O)([O-])O.[Na+]>CN(C)P(=O)(N(C)C)N(C)C>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:6]2[O:5][CH2:4][CH:3]([CH2:2][C:15]#[N:16])[O:8][C:7]=2[CH:9]=1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 18177463HCID 18177463, compound

Product 1

HCID 18177409HCID 18177409, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

1.35 g (4.43 mmol) of the iodinated compound obtained in Step C and 1.37 g (26.6 mmol) of potassium cyanide are dissolved in 15 ml of anhydrous hexamethylphosphoric triamide; the reaction mixture is then stirred for 2 days under argon and at ambient temperature. The solution is then hydrolysed with a solution of sodium hydrogen carbonate; the aqueous phase is then extracted with dichloromethane. The organic phase, dried over magnesium sulphate and then filtered, is concentrated under reduced pressure. The title nitrile is obtained pure in the form of a clear oil after chromatography on silica gel (eluant: PE then AcOEt/PE: 15/85).

Workup

  1. extractionthe aqueous phase is then extracted with dichloromethane
  2. dry with materialThe organic phase, dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-c567ef1f45874c52bf33b9568dd38091
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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