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Lithium Chloride → 2-Phenyl-3-methyl-8-vinylquinoline

HRID 1167179
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1167179
[Cl-].[Li+].[CH2:3](C([Sn])=C(CCCC)CCCC)[CH2:4]CC.[C:18]1([C:24]2[C:33]([CH3:34])=[CH:32][C:31]3[C:26](=[C:27](OS(C(F)(F)F)(=O)=O)[CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]1([C:24]2[C:33]([CH3:34])=[CH:32][C:31]3[C:26](=[C:27]([CH:3]=[CH2:4])[CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 433294Lithium ChlorideHCID 155214792-Phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinolineHCID 53438229Tri(butyl)vinyltin

Produkt 1

HCID 229959252-Phenyl-3-methyl-8-vinylquinolineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

6.3 g (150 mmol) of lithium chloride, 16.8 ml (57 mmol) of tributylvinyltin and 1.6 g (1.5 mmol) of Pd(PPh3)4 are added sequentially at ambient temperature to a solution of 17.7 g (48 mmol) of 2-phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinoline in 250 ml of dioxane, degassed beforehand using a stream of nitrogen. The reaction medium is then heated at 110° C. for 16 hours. After evaporating the dioxane, the residue is taken up in 200 ml of water and 200 ml of ethyl acetate. The aqueous phase is extracted with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7) to provide 11.3 g of 2-phenyl-3-methyl-8-vinylquinoline in the form of a colorless oil. (Yield: 96%)

Aufarbeitung

  1. customdegassed
  2. customAfter evaporating the dioxane
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7)

Quellen und Nachweise

ORD-Eintrag
ord-3b7055f1a163408db7d21a694642bc11
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06617336B1

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