Cyclohexanol → 5-Bromo-2-(cyclohexyloxy)pyridine

HRID 2035836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2035836
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Br:10][C:11]1[CH:12]=[CH:13][C:14](Cl)=[N:15][CH:16]=1>CN(C)C(=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 27344145-Bromo-2-chloropyridine

Produkt 1

HCID 613756815-Bromo-2-(cyclohexyloxy)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

Cyclohexanol (3.99 mL) was added to a mixture of NaH (60%, 1.50 g) in N,N-dimethylacetoamide (10 mL) at 0° C. The mixture was stirred at room temperature for 30 min. The solution of 5-bromo-2-chloropyridine (6.00 g) in N,N-dimethylacetoamide (10 mL) was added and the mixture was stirred at 100° C. for 1.5 hr. The mixture was quenched with water at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (7.67 g) as colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred at 100° C. for 1.5 hr
  2. customThe mixture was quenched with water at room temperature
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-23af448ad9d645f4a74e2e41a96cc787
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575154B2

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