Water → 2-Chloro-5-methoxy-3-methylpyridine

HRID 1758496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758496
[H-].[Na+].[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[CH:6][N:5]=1.[CH3:12]I.O>CN(C=O)C>[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([O:11][CH3:12])=[CH:6][N:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128520156-Chloro-5-methylpyridin-3-ol

Produkt 1

HCID 128520162-Chloro-5-methoxy-3-methylpyridineAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Into a flame dried flask under N2 was placed DMF (150 mL), NaH (50% oil dispersion, 4.0 g, 0.08 mol) and 2-chloro-5-hydroxy-3-methylpyridine (11.7 g, 0.08 mol). The solution was stirred at 0°-5° C. until the evolution of H2 ceased and then a solution of CH3I (5.6 mL, 0.09 mol) in DMF (50 mL) was added dropwise. After the addition, the solution was allowed to stir at room temperature overnight. The resulting slurry was added to H2O and extracted with Et2O (3X). The organic layer was concentrated and the residue distilled at 85° C. (0.6 mm) to yield 12.8 g of 2-chloro-5-methoxy-3-methylpyridine (95%) as an oil; 1H NMR (CDCl3) δ 2.35 (3H, s), 3.8 (3H, s), 7.1 (1H, d, J=3) and 7.9 (1H, d, J=3 ); MS m/e (M+) 157.

Aufarbeitung

  1. customInto a flame dried flask under N2
  2. additionAfter the addition
  3. stirringto stir at room temperature overnight
  4. extractionextracted with Et2O (3X)
  5. concentrationThe organic layer was concentrated
  6. distillationthe residue distilled at 85° C. (0.6 mm)

Quellen und Nachweise

ORD-Eintrag
ord-89b3b1036985477db78a999b171f91f2
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04374140

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