Water → 5-Methoxy-2-methylpyridine

HRID 2387007Notes

Reaction equation

HRID 2387007 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[OH-].[K+].[CH3:11]I.O>CS(C)=O>[CH3:11][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

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

Product 1

HCID 133587775-Methoxy-2-methylpyridineYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Hydroxy-2-methylpyridine (15 g, 0.14 mol) was added to a stirred suspension of KOH (31 g, 0.55 mol) in DMSO (150 mL). The mixture was stirred for 1 hour and then treated with methyl iodide (9.8 mL, 0.15 mol). After 20 mins the reaction mixture was poured into H2O and extracted with ether. The ether extracts were dried over MgSO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 50% EtOAc in hexanes) gave the product as a clear oil (10.1 g, 59%). 1H NMR (400 MHz, CDCl3): δ 2.49 (s, 3 H), 3.83 (s, 3 H), 7.06 (d, J=8.6 Hz, 1 H), 7.12 (d, J=8.3 Hz, 1 H), 8.19 (d, J=2.8 Hz, 1 H).

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether extracts were dried over MgSO4
  3. concentrationconcentrated to a red oil
  4. customPurification by flash column chromatography (0% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-77dabc58943447d28d501ec1de34aa45
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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