Trimethylaluminum → 1-(1-Ethylpropyl)-5-methyl-3-(methylthio)-2 (1H)-pyrazinone

HRID 2251004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251004
Br[C:2]1[N:3]=[C:4]([S:14][CH3:15])[C:5](=[O:13])[N:6]([CH:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:7]=1.[CH3:16][Al](C)C>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:9]([CH:8]([N:6]1[CH:7]=[C:2]([CH3:16])[N:3]=[C:4]([S:14][CH3:15])[C:5]1=[O:13])[CH2:11][CH3:12])[CH3:10]

Komponenten

5

Edukt 2

HCID 16682925TrimethylaluminumHCID 588451705-bromo-1-(1-ethylpropyl)-3-(methylthio)-2 (1H)-pyrazinone

Produkt 1

HCID 588451711-(1-Ethylpropyl)-5-methyl-3-(methylthio)-2 (1H)-pyrazinoneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of XXXI (2.0 g, 6.9 mmol) and dichlorobis(triphenylphosphine)palladium(II) (484 mg, 0.7 mmol) in THF (40 mL) was treated with trimethylaluminum (6.2 mL, 12.4 mmol, 2M/toluene) dropwise at 0° C. The reaction was refluxed for 4 h, cooled to 0° C. quenched with water (50 mL) and extracted with ethyl acetate (100 mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo to give crude residue. Purification by flash column chromatography (silica, ethyl acetate:hexane 1:1) gave the product XXXII (1.14 g, 73%) as a pale yellow solid.

Aufarbeitung

  1. temperatureThe reaction was refluxed for 4 h
  2. customquenched with water (50 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give crude residue
  8. customPurification by flash column chromatography (silica, ethyl acetate:hexane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c231cc311fa8401ca9cd6ccdc073b0bb
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319100B2

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