4-Fluorobenzonitrile → 4-[2-(6-Methyl-2-pyridyl)ethoxy]benzonitrile

HRID 1194079

Reaktionsgleichung

Reaktionsgleichung von HRID 1194079
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=1.F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[H-].[Na+]>O1CCCC1>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 702836-Methylpyridine-2-ethanol

Produkt 1

HCID 142112794-[2-(6-Methyl-2-pyridyl)ethoxy]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 6-methyl-2-pyridineethanol (97.2 g), p-fluorobenzonitrile (85.8 g) and dry tetrahydrofuran (600 ml) was added 60% sodium hydride in oil (29.0 g) in small portions with ice-cooling and stirring and the mixture was further stirred for 2 hours. The reaction mixture was poured in ice-water and extracted with ethyl ether. The ethyl ether layer was washed with water, dried (MgSO4) and concentrated, and the residue was crystallized from hexane to give 4-[2-(6-methyl-2-pyridyl)ethoxy]benzonitrile. Yield: 85.9 g (50.1%); m.p.: 66°-67° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 2 hours
  3. extractionextracted with ethyl ether
  4. washThe ethyl ether layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue was crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-f366beb19d154d3e90f16d539c878b91
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04812570

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