Hydrochloric Acid → HCID 57198439, Verbindung
Reaktionsgleichung
[CH2:1]([O:3][C:4]([CH2:6][C:7](=[O:28])[CH:8]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[H-].[Na+].[CH:31](=O)[CH2:32][CH2:33][CH2:34][CH3:35].Cl>O1CCCC1.O>[O:28]=[C:7]([CH:8]=[CH:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 45 °C
Versuchsvorschrift
To a solution of (3-ethoxycarbonyl-2-oxopropylidene)triphenylphosphorane (5.0 g, 12.8 mmol) in tetrahydrofuran (THF, 50 ml) were added sodium hydride (60% dispersion in oil, 1.03 g, 25.6 mmol) and then pentanal (1.10 g, 12.8 mmol) followed by stirring. After addition of water (three drops), the mixture was heated at 45° C. for 1 hour. The reaction mixture was treated with dilute hydrochloric acid and extracted with ether. The organic layer was washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride, dried (MgSO4), and concentrated to dryness. The resulting residue was purified by column chromatography on silica gel. The column was eluted with dichloromethane-hexane (1:1 to 3:2) to give 1.02 g (40.0%) of the title compound as an oil. The 1H-NMR spectrum indicates that the product is a mixture of keto/enol isomers.
Aufarbeitung
- extractionextracted with ether
- washThe organic layer was washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride
- dry with materialdried (MgSO4)
- concentrationconcentrated to dryness
- customThe resulting residue was purified by column chromatography on silica gel
- washThe column was eluted with dichloromethane-hexane (1:1 to 3:2)
Quellen und Nachweise
- ORD-Eintrag
- ord-9b52cb9d3c7143298531813b01402c3c
- Quelldatensatz
- uspto-grants-1994_04
- Patentnummer
- US05304565
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