Water → HCID 57682862, compound

HRID 494994Notes

Reaction equation

HRID 494994 reaction equation
[CH2:1]([C:4]1[C:13]2[O:12][C:11](=[O:14])[N:10]([CH3:15])[CH2:9][C:8]=2[CH:7]=[CH:6][C:5]=1[OH:16])[CH:2]=[CH2:3].[C:17](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:4]1[C:13]2[O:12][C:11](=[O:14])[N:10]([CH3:15])[CH2:9][C:8]=2[CH:7]=[CH:6][C:5]=1[O:16][CH3:17])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57682879HCID 57682879, compound

Product 1

HCID 57682862HCID 57682862, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.66 g of 8-allyl-7-hydroxy-3-methyl-3,4-dihydro-2H-1,3-benzoxazin-2-one was dissolved in 6 ml of N,N-dimethylformamide. 0.63 g of potassium carbonate and 0.94 ml of methyl iodide were added to the above solution, and the obtained mixture was then stirred at room temperature overnight under nitrogen atmosphere. Thereafter, 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 sodium thiosulfate aqueous solution, 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. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 0.58 g of the subject compound.

Workup

  1. customso as to separate an organic layer
  2. washThe obtained organic layer was washed with a sodium thiosulfate aqueous solution, 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 purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dcbd1d50f1674fd99001550668685323
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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