Water → 5-Allyloxy-2-methylbenzoxazole

HRID 494926Notes

Reaction equation

HRID 494926 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20].O>CN(C)C=O.C(#N)C.C(OCC)(=O)C>[CH2:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1)[CH:19]=[CH2:18]

Participants

8

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 108880735-Hydroxy-2-methylbenzoxazole

Product 1

HCID 576829095-Allyloxy-2-methylbenzoxazole

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.58 g of 5-hydroxy-2-methylbenzoxazole (publication: Synthesis, 1982, 68-69) was dissolved in 15 ml of N,N-dimethylformamide and 15 ml of acetonitrile. Thereafter, 2.39 g of potassium carbonate and 1.61 ml of allyl bromide were successively added to the reaction solution. Approximately 6 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 water and 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 2.78 g of the subject compound.

Workup

  1. customso as to separate an organic layer
  2. washThe obtained organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution, and then dried 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-a253d1f748e64ae28f1ca281c2de93e5
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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