Dimethylformamide → 2-Methyl-5-(2,2,2-trifluoroethoxy)pyridine

HRID 2041188

Reaktionsgleichung

Reaktionsgleichung von HRID 2041188
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([F:20])([F:19])[F:18].CN(C=O)C>[Na+].[Cl-]>[CH3:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:7][N:6]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridineHCID 678982-Bromo-1,1,1-trifluoroethane

Produkt 1

HCID 235684332-Methyl-5-(2,2,2-trifluoroethoxy)pyridineAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5234Sodium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Add 5-hydroxy-2-methyl-pyridine (3.3 g, 30.6 mmol), potassium carbonate (17 g, 122.4 mmol) and 2-bromo-1,1,1-trifluoroethane (10 g, 61.2 mmol) to a flask containing DMF (60 mL) and heat to 95° C. for 20 h. Cool the mixture, dilute with aqueous 10% NaCl (20 mL) and extract with hexane/EtOAc (1:1, 100 mL). Filter the bi-phasic mixture through Celite®, separate and wash the organic layer with aqueous 10% NaCl (3×50 mL) and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1 to 1:1) to obtain the desired intermediate (4.1 g, 70%).

Aufarbeitung

  1. temperatureCool the mixture
  2. extractionextract with hexane/EtOAc (1:1, 100 mL)
  3. filtrationFilter the bi-phasic mixture through Celite®
  4. customseparate
  5. washwash the organic layer with aqueous 10% NaCl (3×50 mL)
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f5e7139d09b040c898a2776ef25df337
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580780B2

Verknüpfte Notizen

Wird geladen…