Potassium Carbonate → 2-(2-o-Tolyl-chroman-6-yloxy)-thiazole-5-carboxylic acid methyl ester
Reaktionsgleichung
[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:17])[CH:13]=2)[O:8]1.Cl[C:20]1[S:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:28][O:27][C:25]([C:22]1[S:21][C:20]([O:17][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[O:8][CH:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:18])[CH2:16][CH2:15]3)=[N:24][CH:23]=1)=[O:26]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
A suspension of 2-o-Tolyl-chroman-6-ol (2.5 g, 10.4 mmol), methyl 2-chloro-thiazole-5-carboxylate (1.9 g, 10.6 mmol, 1.02 eq) and potassium carbonate (1.9 g, 1.3 eq) in dimethylformamide (30 ml) was stirred at 50° C. for 10 h. The suspension was cooled to room temperature and diluted with water. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with water, dried with sodium sulfate and filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel; ethyl acetate/heptane gradient). The product was obtained as a pale yellow solid (3.87 g, 98%).
Aufarbeitung
- temperatureThe suspension was cooled to room temperature
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic layers washed with water
- dry with materialdried with sodium sulfate
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customThe crude product was purified by column chromatography (silica gel; ethyl acetate/heptane gradient)
Quellen und Nachweise
- ORD-Eintrag
- ord-3dd6e8fbcc7d4118ad95ad1fc471bf44
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08912224B2
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