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Methane → 6-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 1867318
Notes
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Reaction equation

HRID 1867318 reaction equation
[C:1]([C:4]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[C:10](=[O:16])[NH:9][C:8]=2[CH:7]=[C:6]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=1)(=[O:3])[CH3:2].[Se](=O)=[O:26].C.[O:29]1CCO[CH2:31][CH2:30]1>O>[CH2:18]([O:17][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH:2]([O:29][CH2:30][CH3:31])[OH:26])[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[C:10](=[O:16])[NH:9][C:8]=2[CH:7]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 297MethaneHCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 21072863HCID 21072863, compound

Product 1

HCID 210728546-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
-18 °C

Procedure

50.12 g (154 mmol) is 8-acetyl-6-benzyloxy-2,2-dimethylbenzo[1,4]oxazin-3-one is reacted with selenium dioxide as oxidizing agent and activated charcoal in refluxing dioxane and some water. After cooling, the solid is filtered off and washed with dioxane. The filtrate is evaporated down and the residue is dissolved in 550 mL of ethanol and refluxed for 30 minutes. It is filtered and the mother liquor is cooled to −18° C., during which time a solid is precipitated which is suction filtered. After recrystallization from ethanol, the product is obtained in the form of a beige solid. Yield: 8.95 g (15%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid is filtered off
  3. washwashed with dioxane
  4. customThe filtrate is evaporated down
  5. dissolutionthe residue is dissolved in 550 mL of ethanol
  6. temperaturerefluxed for 30 minutes
  7. filtrationIt is filtered
  8. customis precipitated which
  9. filtrationfiltered
  10. customAfter recrystallization from ethanol
  11. customthe product is obtained in the form of a beige solid

Sources & evidence

ORD record
ord-281a4ce168fc482790aec91da175f77c
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07632834B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes