5-Ethoxyoxazole → Dimethyl 5-hydroxypyridine-3,4-dicarboxylate

Reaktionsgleichung

[C:1]([O:9][CH3:10])(=[O:8])/[CH:2]=[CH:3]/[C:4]([O:6][CH3:7])=[O:5].C([O:13][C:14]1O[CH:17]=[N:16][CH:15]=1)C>>[CH3:7][O:6][C:4]([C:3]1[CH:17]=[N:16][CH:15]=[C:14]([OH:13])[C:2]=1[C:1]([O:9][CH3:10])=[O:8])=[O:5]

Komponenten

Edukt 2

HCID 3322265-Ethoxyoxazole

HCID 637568Dimethyl Fumarate

Produkt 1

HCID 15257826Dimethyl 5-hydroxypyridine-3,4-dicarboxylate

Versuchsvorschrift

Dimethyl fumarate (781 mg; 1.1 eq.) was added to 5-ethoxyoxazole (557.3 mg; 4.9 mmol), and the mixture was reacted at 120° C. for 1.5 hours. The reaction residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane 2:1), to give crude crystals of the title compound. Yield: 730 mg (70.2%). The crude crystals were recrystallized from dichloromethane-hexane, to give colorless plates.

Aufarbeitung

customthe mixture was reacted at 120° C. for 1.5 hours
customThe reaction residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane 2:1)

Quellen und Nachweise

ORD-Eintrag: ord-700ec23cf79745269df3f782f824b98b
Quelldatensatz: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05420275

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