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Sodium Acetate → HCID 68782696, Verbindung

HRID 2266452
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2266452
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](OS(C(F)(F)F)(=O)=O)=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([S:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:7]2[CH3:21].C([Si]([O:37][C:38]([O:40][CH3:41])=[CH2:39])(C)C)(C)(C)C.C([O-])(=O)C.[Na+]>CN(C)C=O.C(OCC)(=O)C.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:41][O:40][C:38](=[O:37])[CH2:39][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[C:7]([CH3:21])=[C:8]([S:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:9]([CH3:12])=[N:10]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 517045Sodium AcetateHCID 45644911-(tert-Butyldimethylsilyloxy)-1-methoxyetheneHCID 86631433HCID 86631433, Verbindung

Produkt 1

HCID 68782696HCID 68782696, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumKatalysator
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
Katalysator
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of trifluoromethanesulfonic acid 8-chloro-3-(4-chlorophenylsulfanyl)-2,4-dimethylquinolin-5-yl ester (0.31 g), tert-butyl-(1-methoxyvinyloxy)dimethyl silane (0.71 mL), sodium acetate (0.064 g), bis(dibenzylideneacetone) palladium (0.018 g) and 1,1′-bis(diphenylphospino) ferrocene (0) (0.018 g) in N,N-dimethylformamide (4.0 mL) was heated by microwave irradiation at 120° C. for 15 minutes. The mixture was diluted with ethyl acetate, and this solution was washed with saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane and cyclohexane (1:1 to 2:0 by volume) gave title compound as a pale yellow solid, 0.15 g.

Aufarbeitung

  1. washthis solution was washed with saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  4. washeluting with a mixture of dichloromethane and cyclohexane (1:1 to 2:0 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-b608b298808f4739a6d2622055a05eaa
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07858640B2

Notizen zur Reaktion

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