Water → Ethyl 2-[(E)-2-(2-quinolinyl)ethenyl]-1,3-thiazole-4-carboxylate

HRID 907381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907381
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11]P(=O)(OCC)OCC.[H-].[Na+].[CH:22]([C:24]1[S:25][CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=1)=O.O>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:22]/[C:24]1[S:25][CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11011347Diethyl 2-quinolinylmethylphosphonateHCID 11355896Ethyl 2-formyl-1,3-thiazole-4-carboxylate

Produkt 1

HCID 42611537Ethyl 2-[(E)-2-(2-quinolinyl)ethenyl]-1,3-thiazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Diethyl 2-quinolinylmethylphosphonate (0.580 g, 2.08 mmol; see Preparation 13(i) above) was dissolved in anhydrous THF (2 mL), NaH (0.273 g, 11 mmol) was then added in small portions and the resulting solution allowed to stir for 10 min. Ethyl 2-formyl-1,3-thiazole-4-carboxylate (0.387 g, 2.08 mmol; see step (v) above) in anhydrous THF (3 mL) was added dropwise and the solution allowed to stir for 16 h. Water (5 mL) was then added (dropwise initially), during which time the sub-title compound precipitated as a light brown/yellow solid.

Aufarbeitung

  1. stirringto stir for 16 h

Quellen und Nachweise

ORD-Eintrag
ord-633bdbb05e2b4b42881bc7135d4072e8
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012967B2

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