Dimethylformamide → Methyl 5-(5-methyl-2-phenyl-4-oxazolyl)methoxy-3-pyridinecarboxylate

HRID 349950

Reaktionsgleichung

Reaktionsgleichung von HRID 349950
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=1.Cl[CH2:13][C:14]1[N:15]=[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:17][C:18]=1[CH3:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:19][C:18]1[O:17][C:16]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:15][C:14]=1[CH2:13][O:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Produkt 1

HCID 17861341Methyl 5-(5-methyl-2-phenyl-4-oxazolyl)methoxy-3-pyridinecarboxylateAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of methyl 5-hydroxy-3-pyridinecarboxylate (9.84 g), 4-chloromethyl-5-methyl-2-phenyloxazole (13.40 g), potassium carbonate (8.90 g) and N,N-dimethylformamide (100 ml) was stirred at 80° C. overnight. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain methyl 5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridinecarboxylate (12.42 g, yield 59%) as pale yellow crystals from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 119–120° C.

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4b6f402531fb40e68251360b27c030a2
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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