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Methyltriphenylphosphonium chloride → HCID 67317831, Verbindung

HRID 1013738
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1013738
[Cl-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH3:27][O:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([C:39]([C:41]3[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=3)=O)=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1>C1COCC1>[CH3:27][O:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([C:39]([C:41]3[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=3)=[CH2:2])=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 9879809Methyltriphenylphosphonium chlorideHCID 67317464HCID 67317464, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 67317831HCID 67317831, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of methyltriphenylphosphonium chloride (0.54 g, 1.7 mmol) in THF (10 mL) at −78° C. was added n-butyllithium, 2.5 M in hexanes (0.80 ml, 2.0 mmol). After 20 min, a mixture of (7-methoxyquinolin-4-yl)(4-nitrophenyl)methanone (0.177 g, 0.57 mmol) in THF (5 mL) was slowly added. After 10 min, the mixture was allowed to warm to RT. The reaction was quenched with saturated aqueous NH4Cl. The mixture was diluted with EtOAc and washed with water and brine. After drying the organic fraction with Na2SO4, the solvent was removed in vacuo and the residue purified by silica gel chromatography using 40-100% hexanes:EtOAc to afford 7-methoxy-4-(1-(4-nitrophenyl)vinyl)quinoline as a yellow foam. MS: M+H+=307.1.

Aufarbeitung

  1. additionwas slowly added
  2. waitAfter 10 min
  3. customThe reaction was quenched with saturated aqueous NH4Cl
  4. additionThe mixture was diluted with EtOAc
  5. washwashed with water and brine
  6. dry with materialAfter drying the organic fraction with Na2SO4
  7. customthe solvent was removed in vacuo
  8. customthe residue purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d87dd181061741268c93c19e6aeb6044
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07981891B2

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