Dimethylformamide → 3-Chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridine

HRID 81646

Reaktionsgleichung

Reaktionsgleichung von HRID 81646
[C:1](=O)([O-])[O-].[Cs+].[Cs+].BrC[CH2:9][CH:10]1O[CH2:13][CH2:12][O:11]1.CN(C)[CH:17]=[O:18].[Cl:20][C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[N:25][C:26]=1[F:27]>O>[Cl:20][C:21]1[C:26]([F:27])=[N:25][CH:24]=[C:23]([O:28][CH2:9][CH:10]([O:18][CH2:17][CH3:1])[O:11][CH2:12][CH3:13])[CH:22]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 224515553-Chloro-2-fluoro-5-hydroxypyridine

Produkt 1

HCID 684276023-Chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Cesium carbonate (2.9 g, 8.9 mmol) and 2-(2-bromoethyl)-1,3-dioxolane (990 mg, 5.0 mmol) were added to an N,N-dimethylformamide suspension (10 ml) of 5-chloro-6-fluoropyridin-3-ol (570 mg, 3.9 mmol), and stirred at 100° C. for 4 hours. The reaction solution was cooled to room temperature, water was added, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30) to obtain 3-chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridine (640 mg, yield: 62%) as a colorless oil.

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30)

Quellen und Nachweise

ORD-Eintrag
ord-a35d61c75ba94b3e85d6a391a327ae05
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846700B2

Verknüpfte Notizen

Wird geladen…