Sodium periodate → Quinoxaline-6-carboxaldehyde

HRID 729490Notes

Reaction equation

HRID 729490 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[N:6]2)=C.I([O-])(=O)(=O)=[O:14].[Na+]>O1CCOCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH:1]=[O:14])=[CH:12][CH:11]=2)[N:6]=[CH:7][CH:8]=1

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 451216126-Ethenylquinoxaline

Product 1

HCID 763958Quinoxaline-6-carboxaldehydeYield 68.3%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 6-Vinyl-quinoxaline (0.68 g, 4.35 mmol) in dioxane (44 mL) and water (35 mL) was added osmium tetraoxide (2.5% wt in t-BuOH, 2.18 mL, 0.17 mmol) followed by sodium periodate (2.79 g, 13.1 mmol) and the reaction stirred for 3 h. The solution was diluted with ethyl acetate (150 mL) and then washed with water (3×75 mL) followed by brine (75 mL). The organics were dried with magnesium sulfate, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel using 10-20% ethyl acetate in dichloromethane as eluant yielded 470 mg (68% yield) of Quinoxaline-6-carbaldehyde as a white solid. 1H NMR (DMSO-d6): 10.30 (s,1H), 9.11 (d,2H,J=1.9 Hz), 8.74 (d,1H,J=1.4 Hz), 8.26 (m,2H). LC/MS (Method A): r.t.=0.69 min., purity=94.8%, calculated mass=158, [M+H]+=159.

Workup

  1. washwashed with water (3×75 mL)
  2. dry with materialThe organics were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography on silica gel using 10-20% ethyl acetate in dichloromethane as eluant

Sources & evidence

ORD record
ord-ffff54ad20124d66923d6dc541f517f1
Source dataset
uspto-grants-2009_09
Patent number
US07582636B2

Reaction notes

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