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2-Fluoropyridine → 2-{1-Methyl-2-[4-(3,5-difluorophenoxy)phenoxy]ethoxy}pyridine

HRID 1638296
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1638296
[H-].[Na+].[CH3:3][CH:4]([OH:22])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[CH:9][CH:8]=1.[H][H].F[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1>CN(C)C=O.O>[CH3:3][CH:4]([O:22][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:15]=[C:16]([F:21])[CH:17]=[C:18]([F:20])[CH:19]=2)=[CH:11][CH:12]=1
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Komponenten

7

Edukt 4

HCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 134559131-Methyl-2-[4-(3,5-difluorophenoxy)phenoxy]ethanolHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 133867412-{1-Methyl-2-[4-(3,5-difluorophenoxy)phenoxy]ethoxy}pyridineAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (20 mg, 0.5 mmol; 60% in oil) in dimethylformamide (1 ml), a solution of 1-methyl-2-[4-(3,5-difluorophenoxy)phenoxy]ethanol (140 mg, 0.5 mmol) in dimethylformamide (1 ml) was dropwise added with stirring, and stirring was continued at room temperature until the generation of hydrogen gas ceased. 2-Fluoropyridine (97 mg, 1.0 mmol) was dropwise added thereto, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water (40 ml) and extracted with toluene (20 ml) three times. The toluene layer was dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography to give 2-{1-methyl-2-[4-(3,5-difluorophenoxy)phenoxy]ethoxy}pyridine (129 mg) as pale yellow liquid. nD19.0 1.5602.

Aufarbeitung

  1. stirringstirring
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracted with toluene (20 ml) three times
  4. dry with materialThe toluene layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-60471c40b19e4cdea8ebf8b188dc3dfe
Quelldatensatz
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04879292

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