Sodium periodate → (7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehyde

HRID 657157Notes

Reaction equation

HRID 657157 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=C)=[CH:5][CH:4]=1.I([O-])(=O)(=O)=[O:18].[Na+]>CC(O)CC.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=[O:18])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 68810513HCID 68810513, compound

Product 1

HCID 59398142(7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehydeYield 66%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

A mixture of 7-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinoxalinone (1.03 g, 4.75 mmol) and sodium periodate (4.68 g, 21.8 mmol) in 2-butanol (20 mL) and water (40 mL) was treated with osmium tetroxide (4% solution in water, 1.1 mL) and the mixture was stirred for 3.75 h. The butanol was evaporated and the residue was diluted with water and extracted with dichloromethane, then with dichloromethane/THF. The extracts were dried and evaporated, and the residue was chromatographed on silica eluted with 50-100% ethyl acetate/hexane to give the aldehyde (0.68 g, 66%).

Workup

  1. customThe butanol was evaporated
  2. additionthe residue was diluted with water
  3. extractionextracted with dichloromethane
  4. customThe extracts were dried
  5. customevaporated
  6. customthe residue was chromatographed on silica
  7. washeluted with 50-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4a9a8111e57e4cd38a30cf0f7585f13a
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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