Water → 5-Methoxy-2-methylpyridine

HRID 2383520Notes

Reaction equation

HRID 2383520 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1.[CH3:11]I.O>CS(C)=O>[CH3:11][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 142752-Methyl-5-hydroxypyridineHCID 14797Potassium Hydroxide

Product 1

HCID 133587775-Methoxy-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of potassium hydroxide (113 g, 2 mol) in DMSO (800 ml) was added 53.9 g, (0.49 mol) 5-hydroxy-2-methylpyridine and the mixture stirred for 1 h. To this was added CH3I (34 ml, 0.55 mol) and the reaction mixture was stirred for one hour, then poured into water (2400 ml) and extracted with ether (1000 ml×5). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated in vacuo to provide 5-methoxy-2-methylpyridine as a yellow oil. 1H NMR: (400 MHz, CDCl3) δ 8.19 (d, J=2.8 Hz, 1H), 7.14 (dd, J=8.8, 3.8 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 3.83 (s, 3H), 2.65 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred for one hour
  2. extractionextracted with ether (1000 ml×5)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-897ee414bc2942eaa1a8c0d6ac06136e
Source dataset
uspto-grants-2012_09
Patent number
US08263627B2

Reaction notes

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