3-Phenylprop-2-Enal → 2-(2-Hydroxy-4-phenyl-3-buten-1-yl)-6-methylpyrazine

HRID 1587489

Reaktionsgleichung

Reaktionsgleichung von HRID 1587489
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]1[CH:15]=[N:14][CH:13]=[C:12]([CH3:16])[N:11]=1.[CH:17](=[O:26])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[OH:26][CH:17]([CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:9][C:10]1[CH:15]=[N:14][CH:13]=[C:12]([CH3:16])[N:11]=1

Komponenten

5

Edukt 3

HCID 3073-Phenylprop-2-EnalHCID 79382,6-DimethylpyrazineHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 544020952-(2-Hydroxy-4-phenyl-3-buten-1-yl)-6-methylpyrazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a solution of lithium diisopropylamide (1.5 Molar, 73.3 mL, 0.11 mole) in 150 mL of tetrahydrofuran at -78° C. is added slowly a solution of 2,6-dimethylpyrazine (10.8 g, 0.1 mole) in 100 mL of tetrahydrofuran. The mixture is allowed to warm to room temperature and then cooled to -78° C. A solution of cinnamaldehyde (14.5 g, 0.11 mole) in 100 mL of tetrahydrofuran is added dropwise over 15 minutes. The reaction product mixture is then worked up according to the procedures of Example I to provide the title compound.

Aufarbeitung

  1. temperaturecooled to -78° C

Quellen und Nachweise

ORD-Eintrag
ord-2fd2c05a8d0540feb03b78804db9d027
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05218118

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