Sulfoxonium, trimethyl-, iodide (1:1) → HCID 21931845, Verbindung

HRID 1243991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243991
[I-].C[S+](C)(C)=O.[CH2:7]([Li])CCCCC.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH3:26])[C:21](=[O:27])[CH:20]=[CH:19]2>C1COCC1.CCCCCCC>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23]([N:22]([CH3:26])[C:21](=[O:27])[CH:20]3[CH2:7][CH:19]32)=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 2204596-Methoxy-1-methyl-2(1H)-quinolinoneHCID 178506865HCID 178506865, Verbindung

Produkt 1

HCID 21931845HCID 21931845, VerbindungAusbeute 107,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8900HeptaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of 3.35 gm (15.1 mmol) trimethylsulfoxonium iodide in 10 ml of THF at 0° C. under nitrogen was treated portionwise with 5.8 ml (14.6 mmol) of 2.5 M n-hexyllithium in heptane over 30 minutes. The mixture was stirred for 30 minutes at 0° C. and then treated with 1.0 gm (5.02 mmol) 6-Methoxy-1-methyl-1H-quinolin-2-one followed by heating under reflux for 1.5 hours. The reaction mixture was allowed to cool to ambient temperature before quenching with 35 ml of water followed by extraction into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated to afford 1.1 gm of desired product. Mass spectrum APCI m/e 204 (p+1).

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. temperatureto cool to ambient temperature
  4. custombefore quenching with 35 ml of water
  5. extractionfollowed by extraction into ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-64972da0117b461e92952d32eb6b5015
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119207B2

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