Methyl iodide → HCID 22930088, compound

HRID 1296025Notes

Reaction equation

HRID 1296025 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].CI.[C:9]([C:13]1[CH:14]=[C:15]([C:23](=[O:25])[CH3:24])[CH:16]=[C:17]([O:20][CH2:21][CH3:22])[C:18]=1O)([CH3:12])([CH3:11])[CH3:10].[Br-:26].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C.C(Cl)Cl.CO.C(OCC)(=O)C.O>[Br:26][CH2:24][C:23]([C:15]1[CH:16]=[C:17]([O:20][CH2:21][CH3:22])[C:18]([O:4][CH3:1])=[C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:14]=1)=[O:25]

Participants

9

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 23500184Tetra-n-butylammonium tribromideHCID 58910060HCID 58910060, compound

Product 1

HCID 22930088HCID 22930088, compoundYield 88.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Cesium carbonate (662 mg, 2.03 mmol) and methyl iodide (0.14 ml, 2.20 mmol) were added to a solution of 1-[3-(tert-butyl)-5-ethoxy-4-hydroxyphenyl]-1-ethanone (400 mg, 1.69 mmol) in acetonitrile and the mixture was stirred at room temperature for 10 hours. Water was added to the reaction mixture, extraction was performed with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Tetra-n-butylammonium tribromide (841 mg, 1.74 mmol) was added to a solution of the residue in methylene chloride-methanol (8 ml:2 ml) and the mixture was stirred at room temperature for 8 hours. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (491 mg) as a colorless oil.

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. stirringthe mixture was stirred at room temperature for 8 hours
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9f1208269630407a8575ff1d82098f05
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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