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

HRID 1587045Notes

Reaction equation

HRID 1587045 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dbd304cc9bdd4bd896ae40314488c240
Source dataset
uspto-grants-1993_06
Patent number
US05216170

Reaction notes

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