Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:20][O:21][C:22]1[C:27]2[O:28][C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:30]=3[C:26]=2[C:25]([C:38](Cl)=[O:39])=[CH:24][CH:23]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH2:8][C:38]([C:25]1[C:26]2[C:30]3[CH:31]=[C:32]([N+:35]([O-:37])=[O:36])[CH:33]=[CH:34][C:29]=3[O:28][C:27]=2[C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)=[O:39]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -60 °C
Versuchsvorschrift
A solution of 3,5-dichloro-4-methyl-pyridine (0.593 g, 3.66 mmoles) in tetrahydrofuran (200 mL) is cooled to −60° C. under nitrogen atmosphere. A 1M solution of lithium bis(trimethylsilyl) amide (4.4 mL, 4.4 mmoles) is added dropwise and the resulting mixture is stirred at −60° C. for 30 minutes. A solution of 4-methoxy-8-nitro-dibenzofuran-1-carbonyl chloride (3a) (0.75 g, 2.44 mmoles) in dry tetrahydrofuran (20 mL) is added dropwise, maintaining the temperature below −60° C. After stirring for 15 minutes at −60° C., the mixture is stirred at room temperature for 3.5 hours. The mixture is then quenched with a saturated NH4Cl solution (20 mL); the product precipitated as a solid which is recovered by filtration and washed with methanol to yield 340 mg of the title compound.
Aufarbeitung
- temperaturemaintaining the temperature below −60° C
- stirringAfter stirring for 15 minutes at −60° C.
- stirringthe mixture is stirred at room temperature for 3.5 hours
- customThe mixture is then quenched with a saturated NH4Cl solution (20 mL)
- customthe product precipitated as a solid which
- filtrationis recovered by filtration
- washwashed with methanol
Quellen und Nachweise
- ORD-Eintrag
- ord-0f7d5c369b52429c9bd9f24cb6b21a6e
- Quelldatensatz
- uspto-grants-2011_06
- Patentnummer
- US07968724B2
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