Sodium hydride → 4-(4-Fluoro-pyridin-2-yloxymethyl)-benzonitrile

HRID 1891660

Reaktionsgleichung

Reaktionsgleichung von HRID 1891660
Cl[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][N:3]=1.[OH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.[H-].[Na+]>CN(C)C=O>[F:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([O:9][CH2:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 160549p-Cyanobenzyl alcoholHCID 27827922-Chloro-4-fluoropyridine

Produkt 1

HCID 592552704-(4-Fluoro-pyridin-2-yloxymethyl)-benzonitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To an N,N-dimethylformamide (15 mL) solution of 2-chloro-4-fluoropyridine (2.88 g, 21.9 mmol) and 4-(hydroxymethyl)benzonitrile (4.37 g, 32.9 mmol) was added sodium hydride (1.29 g, 32.9 mmol, 60% in oil) at room temperature. This mixture was stirred for 4 hours at 70° C. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (4.08 g, 82%).

Aufarbeitung

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-2790c4bf258d46cda547af7bdec054d2
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507530B2

Verknüpfte Notizen

Wird geladen…