Dimethylformamide → 3-Bromo-5-(methoxymethyl)pyridine

HRID 340472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340472
[H-].[Na+].[CH3:3]N(C=O)C.[Br:8][C:9]1[CH:10]=[C:11]([CH2:15][OH:16])[CH:12]=[N:13][CH:14]=1.CI>O>[Br:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11]([CH2:15][O:16][CH3:3])[CH:10]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Produkt 1

HCID 186245693-Bromo-5-(methoxymethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydride (61% in oil) (11 mg) was added to a DMF (0.9 ml) solution containing (5-bromopyridin-3-yl)methanol (34 mg) under ice cooling, followed by stirring for 1 hour. Then, methyl iodide (17 μl) was added, followed by stirring at room temperature for 13 hours. Thereafter, water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 1:1), and a light yellow solid of 3-bromo-5-(methoxymethyl)pyridine (26.5 mg) was thus obtained.

Aufarbeitung

  1. stirringby stirring at room temperature for 13 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationSubsequently, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-eed2cc3d6dfb422cbb630b89fb5ffbf3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895585B2

Notizen zur Reaktion

Wird geladen…