2-Methyl-5-hydroxypyridine → 5-(2-Ethoxyethoxy)-2-methylpyridine

HRID 1587045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587045
C[O-].[Na+].[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1.C1(C)C=CC(S(O[CH2:22][CH2:23][O:24][CH2:25][CH3:26])(=O)=O)=CC=1>CO>[CH2:23]([O:24][CH2:25][CH2:26][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1)[CH3:22]

Komponenten

5

Edukt 3

HCID 142752-Methyl-5-hydroxypyridineHCID 41253902-Ethoxyethyl 4-methylbenzene-1-sulfonateHCID 10942334Sodium Methoxide

Produkt 1

HCID 150671045-(2-Ethoxyethoxy)-2-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel3×

Versuchsvorschrift

A solution of 994 g (18.4 mmol) of sodium methylate in 20 ml of abs. methanol is added dropwise to a solution of 2 g (18.4 mmol) of 5-hydroxy-2-methylpyridine in 20 ml of abs. methanol. The mixture is stirred for 5 minutes and then a solution of 5.83 g (23. 9 mmol) of (2-ethoxy)ethyl p-toluenesulphonate in 15 ml of abs. methanol is added. The mixture is heated under reflux for 72 hours. It is evaporated to dryness, the residue is taken up in ethyl acetate and washed with saturated NaCl solution. Drying over sodium sulphate and evaporation result in 2.1 g (70% of theory) of a pale yellow oil. 1NMR (CDCl3, δ[ppm]): 1.2 (t, 3H); 2.5 (s, 3H); 3.6 (q, 2H); 3.8 (m, 2H); 4.15 (m, 2H); 7.05 (d, 1H); 7.15 (dd, 1H); 8.2 (d, 1H).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 72 hours
  3. customIt is evaporated to dryness
  4. washwashed with saturated NaCl solution
  5. dry with materialDrying over sodium sulphate and evaporation
  6. customresult in 2.1 g (70% of theory) of a pale yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-dbd304cc9bdd4bd896ae40314488c240
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05216170

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