Dimethylformamide → (4-(Pyridin-2-yloxymethyl)-phenyl)-methanol

HRID 557259

Reaktionsgleichung

Reaktionsgleichung von HRID 557259
[C:1]1([CH2:9][OH:10])[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.CN(C)C=O.[H-].[Na+]>O>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([CH2:9][OH:10])=[CH:2][CH:3]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 97462-FluoropyridineHCID 115061,4-BenzenedimethanolHCID 24758Sodium hydride

Produkt 1

HCID 59255473(4-(Pyridin-2-yloxymethyl)-phenyl)-methanolAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of 1,4-benzenedimethanol (5.5 g, 40 mmol), 2-fluoropyridine (1.3 g, 13 mmol), and N,N-dimethyl formamide (15 mL) was added sodium hydride (1.4 g, 40 mmol, 66% in oil) at 0° C, which was stirred at room temperature for 20 minutes and at 70° C for one hour. To the reaction mixture was added water, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride water, and the solvent thereof was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1) to obtain the title compound (1.9 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride water
  3. customthe solvent thereof was evaporated under a reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-e656e60029c0476ab312e1135b11d455
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058444B2

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