Methyl iodide → HCID 57839108, compound

HRID 733156Notes

Reaction equation

HRID 733156 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[OH:7][C:8]([CH2:22][CH2:23][CH3:24])=[CH:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)=[O:11].IC>CC(C)=O>[CH3:1][CH:9]([C:8](=[O:7])[CH2:22][CH2:23][CH3:24])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178450551HCID 178450551, compound

Product 1

HCID 57839108HCID 57839108, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of potassium carbonate (596 mg) in acetone (7 mL), was added 3-hydroxy-1-(3-trifluoromethylphenyl)-hex-2-en-1-one (190 mg) followed by iodomethane (0.45 mL). The mixture was heated at reflux for 6 h, cooled to room temperature, and the solvent evaporated at reduced pressure. The resulting oil was dissolved in ethyl acetate (20 mL), washed with water (3×20 mL), dried over sodium sulphate and evaporated at reduced pressure to give the crude product as an oil. Flash silica chromatography afforded 2-methyl-1-(3-trifluoromethylphenyl)-hexane-1,3-dione as an oil (102 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 h
  3. customthe solvent evaporated at reduced pressure
  4. dissolutionThe resulting oil was dissolved in ethyl acetate (20 mL)
  5. washwashed with water (3×20 mL)
  6. dry with materialdried over sodium sulphate
  7. customevaporated at reduced pressure
  8. customto give the crude product as an oil

Sources & evidence

ORD record
ord-9cff2dbb65c94098aa23e79d1d744ed1
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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