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Methane → 5-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 969453
Notes
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Reaction equation

HRID 969453 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[C:7]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Se](=O)=O.C.[OH2:29].[O:30]1CCO[CH2:32][CH2:31]1>>[CH2:18]([O:17][C:7]1[C:8]2[NH:9][C:10](=[O:16])[C:11]([CH3:15])([CH3:14])[O:12][C:13]=2[C:4]([C:1](=[O:3])[CH:2]([O:30][CH2:31][CH3:32])[OH:29])=[CH:5][CH:6]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 297MethaneHCID 962WaterHCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 694623038-acetyl-5-benzyloxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 590172615-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Procedure

9.6 g (30 mmol) 8-acetyl-5-benzyloxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one, 3.3 g (30 mmol) selenium dioxide and activated charcoal are stirred for 7 hours in 90 mL dioxane and 2 mL water at reflux temperature. The solid is suction filtered, the filtrate is evaporated down and the residue is refluxed for 30 minutes in 100 ml of ethanol. The solvent is distilled off and the residue is dissolved in 125 mL ethyl acetate. It is extracted successively with potassium carbonate solution and water, dried with sodium sulphate and evaporated down. The oil remaining (10.1 g) is further reacted directly.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated down
  3. temperaturethe residue is refluxed for 30 minutes in 100 ml of ethanol
  4. distillationThe solvent is distilled off
  5. dissolutionthe residue is dissolved in 125 mL ethyl acetate
  6. extractionIt is extracted successively with potassium carbonate solution and water
  7. dry with materialdried with sodium sulphate
  8. customevaporated down
  9. customis further reacted directly

Sources & evidence

ORD record
ord-024ca60da1444369a28f002d212879ce
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07307076B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes