Methyl Benzoate → 1-Phenyl-2-pyrazin-2-yl ethanone

HRID 401160

Reaktionsgleichung

Reaktionsgleichung von HRID 401160
C(NC(C)C)(C)C.[Li]CCCC.[CH3:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1.[C:20](OC)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[C:21]1([C:20](=[O:27])[CH2:13][C:14]2[CH:19]=[N:18][CH:17]=[CH:16][N:15]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 7150Methyl BenzoateHCID 7912DiisopropylamineHCID 79762-MethylpyrazineHCID 178418339Butyllithium

Produkt 1

HCID 5209771-Phenyl-2-pyrazin-2-yl ethanoneAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a mixture of diisopropyl-amine (1.29 g, 12.7 mmol) in anhydrous THF (10 mL) was added n-BuLi (2.5 M/L in hexane, 4.7 mL, 11.7 mmol) at −78° C., after being stirred for 30 minutes, a solution of 2-methylpyrazine (1 g, 10.6 mmol) in THF (5 mL) was added, and the mixture was stirred at −78° C. for 30 minutes, a solution of methyl benzoate (1.4 g, 10.6 mmol) in THF (5 mL) was added, and the mixture was stirred at this temperature for 3 hours. When TLC indicated that the starting material was consumed, the reaction mixture was diluted with EtOAc, and the mixture was washed with water and brine, and concentrated. The residue was purified by column chromatography (PE:EtOAc=30:1) to give Intermediate 26 (700 mg, yield 33.3%).

Aufarbeitung

  1. stirringthe mixture was stirred at −78° C. for 30 minutes
  2. stirringthe mixture was stirred at this temperature for 3 hours
  3. customwas consumed
  4. additionthe reaction mixture was diluted with EtOAc
  5. washthe mixture was washed with water and brine
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (PE:EtOAc=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-26abdd557f50405497b6d8bb48062aea
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741915B2

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