Water → HCID 57682926, compound

HRID 494927Notes

Reaction equation

HRID 494927 reaction equation
[CH2:1]([C:4]1[C:9]2[N:10]=[C:11]([CH3:13])[O:12][C:8]=2[CH:7]=[CH:6][C:5]=1[OH:14])[CH:2]=[CH2:3].[C:15](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O.C(#N)C.C(OCC)(=O)C>[CH2:1]([C:4]1[C:9]2[N:10]=[C:11]([CH3:13])[O:12][C:8]=2[CH:7]=[CH:6][C:5]=1[O:14][CH3:15])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57682924HCID 57682924, compound

Product 1

HCID 57682926HCID 57682926, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.44 g of 4-allyl-5-hydroxy-2-methylbenzoxazole was dissolved in 5 ml of N,N-dimethylformamide and 5 ml of acetonitrile. Thereafter, 1.05 g of potassium carbonate and 0.55 ml of methyl iodide were successively added to the reaction solution. Approximately 16 hours later, water and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The obtained organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, and the residue was then purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 1.26 g of the subject compound.

Workup

  1. customso as to separate an organic layer
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the drying agent
  5. filtrationby filtration
  6. concentrationthe organic layer was concentrated under a reduced pressure
  7. customthe residue was then purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4e028658738045d78305aba37a4b8d32
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

Loading…