Reaktionsgleichung
[CH2:1]([O:4][CH3:5])[C:2]#[CH:3].C([Li])CCC.CCCCCC.[CH3:17][N:18]([CH3:32])[C:19]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1.[Br-].[Li+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O.CS(C)=O.C1COCC1>[CH2:35]([O:25][C:22]1([C:3]#[C:2][CH2:1][O:4][CH3:5])[CH2:23][CH2:24][C:19]([N:18]([CH3:32])[CH3:17])([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:20][CH2:21]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1Komponenten
Edukt 6
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- -5 °C
Versuchsvorschrift
Methyl propargyl ether (0.36 g, 5.2 mmol) dissolved in abs. THF (5 mL) was added in drops to a 2.5 M solution of butyl lithium in hexane (2.1 mL, 5.2 mmol) at −30° C. in argon. A solution of 4-dimethylamino-4-phenylcyclohexanone (1.08 g, 5.0 mmol) in abs. THF (5 mL) and lithium bromide (0.22 g, 2.5 mmol) dissolved in abs. THF (2.0 mL) was then added at −30° C. The reaction mixture was heated to −5° C., mixed in drops with a solution of benzyl bromide (1.28 g, 7.5 mmol) in abs. DMSO (10 mL) and stirred 2 h at 50° C. For work up of the reaction mixture water (10 mL) was added with ice bath cooling and extracted with cyclohexane (4×20 mL). The organic phase was washed with 20% ammonium chloride solution, dried over Na2SO4 and concentrated to low volume in a vacuum. The remaining residue was purified by flash chromatography with CHCl3/MeOH (40:1).
Aufarbeitung
- temperaturecooling
- extractionextracted with cyclohexane (4×20 mL)
- washThe organic phase was washed with 20% ammonium chloride solution
- dry with materialdried over Na2SO4
- concentrationconcentrated to low volume in a vacuum
- customThe remaining residue was purified by flash chromatography with CHCl3/MeOH (40:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-a9aa16dfd7fd4cdfac553552dfcd70be
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08835689B2
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