Cesium carbonate → 2,3-Dichloro-5-(2-methoxyethoxy)pyridine

HRID 81664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81664
[CH3:1][O:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[N:17][C:18]=1[Cl:19].O.[Cl-].[NH4+]>C(OCC)(=O)C.CN(C)C(=O)C>[Cl:19][C:18]1[C:13]([Cl:12])=[CH:14][C:15]([O:20][CH2:4][CH2:3][O:2][CH3:1])=[CH:16][N:17]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 143916722,3-Dichloro-5-hydroxypyridineHCID 57429219Ammonium chloride monohydrate

Produkt 1

HCID 866459022,3-Dichloro-5-(2-methoxyethoxy)pyridineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Bromoethyl methyl ether (0.44 ml, 4.57 mmol) and cesium carbonate (2.48 g, 7.62 mmol) were added to an N,N-dimethylacetamide solution (5 ml) of 5,6-dichloropyridin-3-ol (500 mg, 3.05 mmol), and stirred under a nitrogen atmosphere at 80° C. for 5 hours. The reaction solution was cooled with ice, then ammonium chloride water and ethyl acetate were added, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=9:1) to obtain 2,3-dichloro-5-(2-methoxyethoxy)pyridine (573 mg, yield: 85%) as an orange oil.

Aufarbeitung

  1. temperatureThe reaction solution was cooled with ice
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-32deaa2d4ebe4137b2c57faecb2d6491
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846700B2

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