Methyl 3-formylbenzoate → Methyl 3-[2(E)-(quinolin-2-yl)ethenyl]benzoate
Reaktionsgleichung
C([Li])CCC.[Cl-].[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH2:17][PH3+].[CH:19]([C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25])=O>CCCCCC.O1CCCC1.O>[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1/[CH:17]=[CH:19]/[C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25]Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- -75 °C
Versuchsvorschrift
2.5M Butyl lithium in hexane (8.8 ml) was added over 5 minutes to a stirred solution of quinolin-2-ylmethylphosphonium chloride (9.66 g, 22 mmol) in dry tetrahydrofuran (250 ml) at -75° C. The mixture was stirred for 1 hour at -75° C. then a solution of methyl 3-formylbenzoate (3.28 g, 20 mmol) in tetrahydrofuran (25 ml) was added dropwise over 10 minutes. After stirring for a further 30 minutes at -75° C. the mixture was warmed to room temperature, diluted with water and extracted with ethyl acetate. The extract was dried and evaporated and the residue was purified by chromatography on silica eluting with ethyl acetate-hexane (1:3).
Aufarbeitung
- stirringAfter stirring for a further 30 minutes at -75° C. the mixture
- temperaturewas warmed to room temperature
- extractionextracted with ethyl acetate
- customThe extract was dried
- customevaporated
- customthe residue was purified by chromatography on silica eluting with ethyl acetate-hexane (1:3)
Quellen und Nachweise
- ORD-Eintrag
- ord-bc50303f2be34977a7bdbc289cdd72a0
- Quelldatensatz
- uspto-grants-1994_01
- Patentnummer
- US05281593
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