Lithium diisopropylamide → 5-(9-Ethoxycarbonylnona-6,8-dienyl)imidazo[1,5-a]pyridine

HRID 280207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280207
C([N-]C(C)C)(C)C.[Li+].[CH3:9][CH2:10][O:11][C:12](/[CH:14]=[CH:15]/[CH2:16]P(OCC)(OCC)=O)=[O:13].[CH:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[N:37]2[CH:38]=[N:39][CH:40]=[C:36]2[CH:35]=[CH:34][CH:33]=1)=O>O1CCCC1>[CH2:10]([O:11][C:12]([CH:14]=[CH:15][CH:16]=[CH:25][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[N:37]2[CH:38]=[N:39][CH:40]=[C:36]2[CH:35]=[CH:34][CH:33]=1)=[O:13])[CH3:9]

Komponenten

5

Edukt 3

HCID 2724682Lithium diisopropylamideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 233218905-(5-Formylpentyl)imidazo[1,5-a]pyridine

Produkt 1

HCID 540559275-(9-Ethoxycarbonylnona-6,8-dienyl)imidazo[1,5-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of lithium diisopropylamide (prepared from 3.8 ml of n-butyllithium in hexane and 0.84 ml of diisopropylamine) in 10 ml tetrahydrofuran at -70° C., is added 1.35 g of triethyl 4-phosphonocrotonate in a dropwise manner over a 15 minute period. On completion of the addition, 6.0 g of 5-(5-formylpentyl)imidazo[1,5-a]pyridine is added in a dropwise manner. The reaction mixture is allowed to stir at room temperature for 15 minutes. The reaction mixture is quenched with methanol and the solvent evaporated under reduced pressure to yield 5-(9-ethoxycarbonyl-nona-6,8-dienyl)-imidazo[1,5-a]pyridine as an oil.

Aufarbeitung

  1. additionis added in a dropwise manner
  2. customThe reaction mixture is quenched with methanol
  3. customthe solvent evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5ff47a749feb4f6cabb6e410800777fd
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588732

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