Triethylamine → 4-Bromo-2-((tert-butyldimethylsilyl)oxy)-6-methylpyridine

HRID 1924951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1924951
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([OH:9])[CH:3]=1.[CH3:10][C:11]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][Si:14]([C:11]([CH3:13])([CH3:12])[CH3:10])([CH3:16])[CH3:15])[CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 178422452HCID 178422452, Verbindung

Produkt 1

HCID 590230434-Bromo-2-((tert-butyldimethylsilyl)oxy)-6-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-6-methylpyridin-2-ol (376 mg, 2 mmol) in dry DMF (20 mL) is stirred under N2. TBDMS-Cl (600 mg, 4 mmol) is added, followed by triethylamine (0.97 mL, 7.00 mmol), and the mixture is stirred at rt for 1 h. The solution is poured into ice-water (170 mL) and extracted with diethyl ether (5×50 mL). The combined extracts are dried over Na2SO4 and the solvent is evaporated under reduced pressure. The residue is taken up in pentane (50 mL), dried over Na2SO4 and the solvent evaporated again, to afford the crude title compound as a yellow oil. This is used without further purification.

Aufarbeitung

  1. extractionextracted with diethyl ether (5×50 mL)
  2. dry with materialThe combined extracts are dried over Na2SO4
  3. customthe solvent is evaporated under reduced pressure
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated again

Quellen und Nachweise

ORD-Eintrag
ord-4745503aa2ad4fe787912fc38fbb37b4
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178530B2

Notizen zur Reaktion

Wird geladen…