Methyl iodide → HCID 57614580, compound

HRID 656276Notes

Reaction equation

HRID 656276 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([OH:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:14](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([O:13][CH3:14])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 149548374-tert-Butyl-2-hydroxybenzonitrile

Product 1

HCID 57614580HCID 57614580, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

4-t-Butyl-2-hydroxybenzonitrile (1.16 g) and potassium carbonate (376 mg) were dissolved in dimethylformamide (4 ml) and to the solution was added dropwise iodomethane (226 μl), followed by stirring at 50° C. for 2 hours. The resulting mixture was filtered to remove the remaining potassium carbonate and concentrated under reduced pressure. The obtained residue was purified by column-chromatography (hexane/ethyl acetate=10/1) to yield the compound 13-2a (167 mg, 97%).

Workup

  1. filtrationThe resulting mixture was filtered
  2. customto remove the remaining potassium carbonate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by column-chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-e5581a03fe4743d5a78899d2c927fa95
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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