Methyl iodide → 4-(2,2,2-Trifluoro-1-methoxyethyl)pyridine-2-carbonitrile

HRID 1880764Notes

Reaction equation

HRID 1880764 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1)[OH:4].[C:15](=O)([O-])[O-].[K+].[K+].CI.[Cl-].[NH4+]>CN(C)C=O>[F:14][C:2]([F:1])([F:13])[CH:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1)[O:4][CH3:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 595703134-(2,2,2-Trifluoro-1-hydroxyethyl)pyridine-2-carbonitrile

Product 1

HCID 595703734-(2,2,2-Trifluoro-1-methoxyethyl)pyridine-2-carbonitrileYield 46.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4 ml of dimethylformamide were added 0.4 g of 4-(2,2,2-trifluoro-1-hydroxyethyl)pyridine-2-carbonitrile, 0.33 g of potassium carbonate and 0.34 g of methyl iodide, and the mixture was stirred at room temperature for 20 hours. Thereafter, an aqueous saturated ammonium chloride solution was added to the reaction solution, the resultant solution was extracted with ethyl acetate three times, the organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.2 g of 4-(2,2,2-trifluoro-1-methoxyethyl)pyridine-2-carbonitrile.

Workup

  1. extractionthe resultant solution was extracted with ethyl acetate three times
  2. dry with materialdried with anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-388a4c6435284c00bd9126b5c2a66ade
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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