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Water → (6-methoxy-1-methyl-2-oxo-1,4-dihydro-2H-benz[d][1,3]oxazin-7-yl)acetaldehyde

HRID 494952
Notes
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Reaction equation

HRID 494952 reaction equation
[OH:1][CH:2](CO)[CH2:3][C:4]1[C:5]([O:16][CH3:17])=[CH:6][C:7]2[CH2:12][O:11][C:10](=[O:13])[N:9]([CH3:14])[C:8]=2[CH:15]=1.O.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.CO.C(OCC)(=O)C>[CH3:17][O:16][C:5]1[C:4]([CH2:3][CH:2]=[O:1])=[CH:15][C:8]2[N:9]([CH3:14])[C:10](=[O:13])[O:11][CH2:12][C:7]=2[CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 576828207-(2,3-Dihydroxypropyl)-6-methoxy-1-methyl-1,4-dihydrobenz[d][1,3]oxazin-2-one

Product 1

HCID 57682859(6-methoxy-1-methyl-2-oxo-1,4-dihydro-2H-benz[d][1,3]oxazin-7-yl)acetaldehydeYield 67.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

280 mg of 7-(2,3-dihydroxypropyl)-6-methoxy-1-methyl-1,4-dihydrobenz[d][1,3]oxazin-2-one was dissolved in 4 ml of tetrahydrofuran and 4 ml of methanol. Thereafter, 8 ml of water containing 0.29 g of sodium metaperiodate was added to the reaction solution while cooling on ice, and the obtained mixture was then stirred at room temperature for 30 minutes. The reaction solution was diluted with ethyl acetate and then washed with a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), so as to obtain 167 mg of (6-methoxy-1-methyl-2-oxo-1,4-dihydro-2H-benz[d][1,3]oxazin-7-yl)acetaldehyde.

Workup

  1. temperaturewhile cooling on ice
  2. washwashed with a saturated sodium chloride aqueous solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-999ff8ff60ec47cd963c6a2a559e1f25
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538123B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes