Ammonia → (4-(2-(Pyridin-4-YL)vinyl)phenyl)methanol

HRID 636514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636514
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]2[CH:24]=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.N.CO>O1CCCC1>[N:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:23][CH:24]=2)=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 887MethanolHCID 12006312methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 70240750(4-(2-(Pyridin-4-YL)vinyl)phenyl)methanolAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of lithium aluminum hydride (92.8 mg) in tetrahydrofuran (12 ml) was added methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoate (1.17 g), and after stirring for 2 hours at ambient temperature, ammonia solution and methanol were added thereto. The mixture was stirred for 2 hours at ambient temperature. Insoluble material was filtered off, and the filtrate was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized with diisopropyl ether to give 4-[(E)-2-(4-pyridyl)vinyl]benzyl alcohol (762 mg).

Aufarbeitung

  1. stirringThe mixture was stirred for 2 hours at ambient temperature
  2. filtrationInsoluble material was filtered off
  3. washthe filtrate was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c1be4c4d70c04813941814b32c53aa89
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194396B1

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