Ethyl Acetate → Tert-butyl 5-formylpyrazine-2-carboxylate

HRID 2045861

Reaktionsgleichung

Reaktionsgleichung von HRID 2045861
I([O-])(=O)(=O)=O.[Na+].CN(C)/C=[CH:10]/[C:11]1[N:12]=[CH:13][C:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:15][CH:16]=1.C([O-])(O)=[O:26].[Na+].CCOC(C)=O>C1COCC1.O>[CH:10]([C:11]1[N:12]=[CH:13][C:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:15][CH:16]=1)=[O:26]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 57475684t-butyl 5-((E)-2-dimethylaminovinyl)pyrazine-2-carboxylate

Produkt 1

HCID 57475686Tert-butyl 5-formylpyrazine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

Sodium periodate (1.67 g) was added to a solution of t-butyl 5-((E)-2-dimethylamino-vinyl)-pyrazine-2-carboxylate (645 mg) in 50% THF-water (26 mL), and the mixture was stirred at RT for 4 h. A saturated NaHCO3 solution and EtOAc were added to the reaction solution, and the organic layer was separated. The organic layer was washed with a saturated NaCl solution and dried over anhydrous MgSO4. The insoluble matter was separated by filtration and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain the title compound (249 mg). 1H-NMR (CDCl3) δ (ppm): 1.68 (s, 9H), 9.25 (d, J=1.2 Hz, 1H), 9.36 (d, J=1.6 Hz, 1H), 10.2 (s, 1H).

Aufarbeitung

  1. customthe organic layer was separated
  2. washThe organic layer was washed with a saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. customThe insoluble matter was separated by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-090684305bae42a5b2c12ca0b0750f07
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592408B2

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