Sodium hydride → 2-Methoxy-4-methylpyridine

HRID 647984Notes

Reaction equation

HRID 647984 reaction equation
[H-].[Na+].OC[CH:5]1[O:9][CH:8]([C:10]2[CH:15]=[CH:14]C=CC=2)[N:7]([CH:16]([CH3:18])C)C1.ClC1C=C(C)C=CN=1>CN(C)C=O>[CH3:5][O:9][C:8]1[CH:10]=[C:15]([CH3:14])[CH:18]=[CH:16][N:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 772482-Chloro-4-methylpyridineHCID 125661982-Phenyl-3-isopropyl-5-hydroxymethyloxazolidine

Product 1

HCID 142234722-Methoxy-4-methylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

4.8 g of sodium hydride dispersion (55% strength) are cautiously added in portions to a solution of 27.5 g of 5-hydroxymethyl-3-isopropyl-2-phenyl-oxazolidine in 100 ml of dimethylformamide at 20°-40° C. and after foaming has ceased the mixture is stirred for a further 1-2 hours at 40° C. 12.7 g of 2-chloro-4-methyl-pyridine are then added and the reaction mixture is stirred for 2 hours at 80° C. After evaporating off the solvent in vacuo, the evaporation residue is taken up in ether and the ether solution is washed with water, dried over magnesium sulphate and evaporated in vacuo. Crude 2-[3'-isopropyl]-2'-phenyl-oxazolidinyl-(5')]-methoxy-4-methyl-pyridine is thus obtained.

Workup

  1. stirringthe reaction mixture is stirred for 2 hours at 80° C
  2. customAfter evaporating off the solvent in vacuo
  3. washthe ether solution is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-05f2083f77754e04bea7357ae42a2194
Source dataset
uspto-grants-1983_10
Patent number
US04410530

Reaction notes

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