Water → 5-Methoxy-2-methylpyridine

HRID 1438196Notes

Reaction equation

HRID 1438196 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, 3H), 3.83 (s, 3H), 7.06 (d, J=8.6 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H), 8.19 (d, J=2.8 Hz, 1H).

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-1b2164d1f7fe47f48bffa0a006e77445
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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