Sodium periodate → Ethyl 5-formyl-4-methylisoxazole-3-carboxylate

HRID 1478208

Reaktionsgleichung

Reaktionsgleichung von HRID 1478208
[CH3:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][O:5][C:6]=1[CH:7]=C.I([O-])(=O)(=O)=[O:15].[Na+]>C1COCC1.O.[Os]>[CH:7]([C:6]1[O:5][N:4]=[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]=1[CH3:1])=[O:15]

Komponenten

6

Edukt 2

HCID 23667635Sodium periodateHCID 118511048Ethyl 4-methyl-5-vinylisoxazole-3-carboxylate

Produkt 1

HCID 118511140Ethyl 5-formyl-4-methylisoxazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23937OsmiumKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To ethyl 4-methyl-5-vinylisoxazole-3-carboxylate (3 g, 16.56 mmol) in THF (40 mL) and water (20 mL) at room temperature, was added sodium periodate (10.62 g, 49.7 mmol) and Osmium ENCAT 40 (828 mg, 0.248 mmol). The reaction mixture was stirred at room temperature over the weekend. The resulting mixture was filtered over Celite® (5 g), washing with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and the solvent was removed under reduced pressure. The crude material was suspended in DCM, sonicated and passed through a phase separating cartridge. The eluent was collected and the solvent removed under reduced pressure to afford the title compound;

Aufarbeitung

  1. filtrationThe resulting mixture was filtered over Celite® (5 g)
  2. washwashing with EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customsonicated
  9. customseparating cartridge
  10. customThe eluent was collected
  11. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-47ca386fff89432fbe149f06e5aca1c5
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403810B2

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