Neopentyl alcohol → 2-Fluoro-6-(neopentyloxy)pyridine

HRID 455695

Reaktionsgleichung

Reaktionsgleichung von HRID 455695
[CH2:1]([OH:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[H-].[Na+].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](F)[N:11]=1>CS(C)=O>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[N:11]=1

Komponenten

5

Edukt 3

HCID 6404Neopentyl alcoholHCID 24758Sodium hydrideHCID 739342,6-Difluoropyridine

Produkt 1

HCID 574756582-Fluoro-6-(neopentyloxy)pyridineAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of neopentyl alcohol (1.065 mL, 9.81 mmol) in DMSO (82 mL) was cooled to 0° C. NaH (60% in mineral oil; 0.490 g, 12.26 mmol) were added in one portion, the reaction mixture was warmed to rt and stirred for 20 minutes. 2,6-Difluoropyridine (0.941 mL, 8.175 mmol) was added and the reaction mixture was stirred at overnight. The reaction mixture was quenched with aqueous, saturated ammonium chloride solution, diluted with water and EtOAc. The organic layer was separated, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to afford 2-fluoro-6-(neopentyloxy)pyridine (1.48 g, 8.08 mmol) as a colorless liquid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at overnight
  2. customThe reaction mixture was quenched with aqueous, saturated ammonium chloride solution
  3. additiondiluted with water and EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6ebbf77db7b74968bc53b4b25510495f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497264B2

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