Water → 6,10-Dimethyl-11-(dimethyl t-butylsilyl)oxy-5,9-undecadien-2-one
Reaktionsgleichung
[C:1]([CH:4]([CH2:9][CH:10]=[C:11]([CH3:26])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:25])[CH2:16][O:17][Si:18]([CH3:24])([CH3:23])[C:19]([CH3:22])([CH3:21])[CH3:20])C(OC)=O)(=[O:3])[CH3:2].[I-].[Na+].O>CN(C)P(=O)(N(C)C)N(C)C>[CH3:26][C:11]([CH2:12][CH2:13][CH:14]=[C:15]([CH3:25])[CH2:16][O:17][Si:18]([CH3:24])([CH3:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:10][CH2:9][CH2:4][C:1](=[O:3])[CH3:2]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
To a solution of methyl 2-acetyl-10-(dimethyl t-butylsilyl)oxy-5,9-dimethyl-4,8-decadienate (96 mg, 0.25 mmol) in hexamethylphosphoric triamide (0.5 ml) were added sodium iodide (45 mg, 0.30 mmol) and water (0.01 ml), and the mixture was stirred at 150° C. After two hours, the reaction mixture was allowed to cool to room temperature, and water (2 ml) was added thereto. The product was extracted with ether (5 mlx2). The extract was dried over Na2SO4, and concentrated to give a residue, which was then purified with silica gel column chromatography to obtain 6,10-dimethyl-11-(dimethyl t-butylsilyl)oxy-5,9-undecadien-2-one (57 mg, 70%).
Aufarbeitung
- temperatureto cool to room temperature
- extractionThe product was extracted with ether (5 mlx2)
- dry with materialThe extract was dried over Na2SO4
- concentrationconcentrated
- customto give a residue, which
- customwas then purified with silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-d9be36632fa2477b81ebde35ae204e7e
- Quelldatensatz
- uspto-grants-1994_10
- Patentnummer
- US05354874
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