Potassium Cyanide → HCID 18177409, compound

HRID 428181Notes

Reaction equation

HRID 428181 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 acid 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 acid
  3. filtrationthen filtered
  4. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-328557fbf2f547299856332b2079afa6
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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