Sodium Cyanide → 2-(6-(2,2,2-Trifluoroethoxy)pyridin-2-yl)acetonitrile

HRID 715392Notes

Reaction equation

HRID 715392 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[N:7]=1.C(=O)([O-])O.[Na+]>CS(C)=O>[F:15][C:14]([F:17])([F:16])[CH2:13][O:12][C:8]1[N:7]=[C:6]([CH2:5][C:1]#[N:2])[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 622388462-(Chloromethyl)-6-(2,2,2-trifluoroethoxy)pyridine

Product 1

HCID 898744142-(6-(2,2,2-Trifluoroethoxy)pyridin-2-yl)acetonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium cyanide (0.823 g, 16.8 mmol) is added to a solution of 2-(chloromethyl)-6-(2,2,2-trifluoroethoxy)pyridine (2.0 g, 7.63 mmol, Step-4) in DMSO (38 mL) and stirred at rt for 20 hours. The reaction mixture is poured into saturated aqueous sodium hydrogen carbonate (60 mL) and extracted with EtOAc (100 mL). The organic layer is washed with water (50 mL×2) and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on amine gel eluting with n-hexane/EtOAc (3:1) to give 1.13 g (69% yield) of the title compound as yellow oil.

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. washThe organic layer is washed with water (50 mL×2)
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe residue is purified by column chromatography on amine gel
  7. washeluting with n-hexane/EtOAc (3:1)

Sources & evidence

ORD record
ord-7ff6af3b9e024262be7e0c9528044d8c
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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