Water → HCID 63196962, compound

HRID 623311Notes

Reaction equation

HRID 623311 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][C:13]([CH3:15])=[O:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:16]I.[OH-].[K+].O>C(COC)OC>[Cl:1][C:2]1[C:3]([CH:12]([CH3:16])[C:13](=[O:14])[CH3:15])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 1490211400077-39-6

Product 1

HCID 63196962HCID 63196962, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

6.00 g of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]acetone (Int-11) (27 mMol) (synthesis according to P10 and comm av.) and 5.75 g of methyl iodide (40.5 mMol) were diluted in 120 mL of dimethoxyethane. 3.03 g of potassium hydroxide were added portionwise at room temperature. After cooling, 100 mL of water were added to the reaction mixture which was extracted twice with 150 mL of ethyl acetate. The organic phase was washed twice with 100 mL of water, dried over magnesium sulfate and concentrated. After purification on silica, 0.67 g (39%) of desired product 3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one (Int-12) were obtained, [M+1]=252.

Workup

  1. temperatureAfter cooling
  2. extractionwas extracted twice with 150 mL of ethyl acetate
  3. washThe organic phase was washed twice with 100 mL of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customAfter purification on silica

Sources & evidence

ORD record
ord-964915823e3247eeac6dd641de389a22
Source dataset
uspto-grants-2016_04
Patent number
US09301526B2

Reaction notes

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