Sodium Iodide → 7-Methoxy-2-(5-methoxyhept-1-y)bicyclo[3.3.0]octane
Reaktionsgleichung
[CH3:1][O:2][CH:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:15][CH2:14][CH:13]2[CH:9]1[CH2:10][CH:11]([OH:16])[CH2:12]2.[I-].[Na+].[CH3:21]I>O1CCCC1>[CH3:21][O:16][CH:11]1[CH2:10][CH:9]2[CH:13]([CH2:14][CH2:15][CH:8]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:17][CH3:18])[CH2:12]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
The starting material, 2-(5-methoxyhept-1-yl)bicyclo[3.3.0]7 octanol {octahydro-4-(5-methoxyheptyl)-2-pentalenol} (1.0 g, 3.9 mmoles) is added to a reaction vessel containing sodium iodide (0.12 g, 4.9 mmoles) and tetrahydrofuran (12 ml). The solution is stirred while methyl iodide (0.84 g, 5.9 mmoles) is rapidly added. The reaction is heated in a 50° C. water bath for 4 hours. The water bath is removed and the reaction neutralized with the addition of water (5 ml). The organic phase is separated and the aqueous phase extracted with ether (2×50 ml). The ether extracts are combined and washed with brine (50 ml). The solution is dried over anhydrous magnesium sulfate and the solvent removed under vacuum leaving a clear yellow oil. The product is then kugelrohred under reduced pressure leaving a pale yellow oil (0.8 g, 3.1 mmoles).
Aufarbeitung
- additionis added to a reaction vessel
- additionis rapidly added
- customThe water bath is removed
- additionthe reaction neutralized with the addition of water (5 ml)
- customThe organic phase is separated
- extractionthe aqueous phase extracted with ether (2×50 ml)
- washwashed with brine (50 ml)
- dry with materialThe solution is dried over anhydrous magnesium sulfate
- customthe solvent removed under vacuum
- customleaving a clear yellow oil
Quellen und Nachweise
- ORD-Eintrag
- ord-84333a5b19d34faba23cff08212dd607
- Quelldatensatz
- uspto-grants-1987_08
- Patentnummer
- US04689345
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