Reaktionsgleichung
[C:1]([NH2:11])(=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1.Br[CH:35]([CH3:43])[C:36](=O)[CH2:37][C:38]([O:40][CH3:41])=[O:39]>O1CCCC1>[CH3:43][C:35]1[S:21][C:1]([CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:11][C:36]=1[CH2:37][C:38]([O:40][CH3:41])=[O:39]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Cinnamamide (3.27 g) was dissolved in tetrahydrofuran (33 ml), and Lawesson's reagent (4.94 g) was added. The mixture was refluxed for 3 h and methyl 4-bromo-3-oxopentanoate (6.97 g) was added. The mixture was further refluxed for 11 h. Tetrahydrofuran was evaporated under reduced pressure and ethyl acetate (300 ml) was added to the obtained residue. The mixture was washed with water (200 ml) and then with saturated brine (200 ml), and dried (Na2SO4). Ethyl acetate was evaporated under reduced pressure and the obtained residue was purified by column chromatography to give methyl (5-methyl-2-styrylthiazole-4-yl)acetate (2.9 g).
Aufarbeitung
- temperatureThe mixture was refluxed for 3 h
- temperatureThe mixture was further refluxed for 11 h
- customTetrahydrofuran was evaporated under reduced pressure and ethyl acetate (300 ml)
- additionwas added to the obtained residue
- washThe mixture was washed with water (200 ml)
- dry with materialwith saturated brine (200 ml), and dried (Na2SO4)
- customEthyl acetate was evaporated under reduced pressure
- customthe obtained residue was purified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-a1c5a391e4c7465e901417098647f6eb
- Quelldatensatz
- uspto-grants-2009_07
- Patentnummer
- US07557123B2
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