Reaktionsgleichung
[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]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 4
Versuchsvorschrift
To a mixture of 6-vinylquinoxaline (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 three hours. 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 to dryness on a rotary evaporator. 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-carboxaldehyde as a white solid. 1H NMR (DMSO-d6): δ=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), rt=0.69 mins., purity=94.8%, calculated mass=158, [M+H]+=159.
Aufarbeitung
- washwashed with water (3×75 mL)
- dry with materialThe organics were dried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness on a rotary evaporator
- customPurification by flash column chromatography on silica gel using 10-20% ethyl acetate in dichloromethane as eluant
Quellen und Nachweise
- ORD-Eintrag
- ord-b0faf59324694ce2a4a08d62e00fc0c7
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07696210B2
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