p-Toluenesulfonic acid → Diethyl 2-ethyloxazolo[5,4-b]pyridine-5,6-dicarboxylate

HRID 1655875

Reaktionsgleichung

Reaktionsgleichung von HRID 1655875
[NH2:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:3]=1.C(O[C:22](OCC)(OCC)[CH2:23][CH3:24])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:23]([C:24]1[O:8][C:7]2[C:2]([N:1]=1)=[CH:3][C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]=2)[CH3:22]

Komponenten

4

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 66995Ethyl orthopropionateHCID 19958246Diethyl 5-amino-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Produkt 1

HCID 19958240Diethyl 2-ethyloxazolo[5,4-b]pyridine-5,6-dicarboxylateAusbeute 84,8 %

Versuchsvorschrift

Diethyl 5-amino-1,6-dihydro-6-oxo-pyridine-2,3-dicarboxylate (7.57 g, 0.030 mol), is suspended in mL triethylorthopropionate (TEOP 0.30 mol). A small amount of p-toluenesulfonic acid is added and the mixture is heated at reflux for 65 hours. The triethylorthopropionate is removed in vacuo and the resulting oil is purified by column chromatography. The tractions containing the pure desired product are combined and stripped to a honey-colored oil weighing 7.38 g, yield 84.8%.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 65 hours
  3. customThe triethylorthopropionate is removed in vacuo
  4. customthe resulting oil is purified by column chromatography
  5. additionThe tractions containing the pure desired product

Quellen und Nachweise

ORD-Eintrag
ord-ef482d8526f84f0ca5ae1d1f10889e77
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05252538

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