Water → 5-Methoxy-2-methylpyridine

HRID 859618Notes

Reaction equation

HRID 859618 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-56d6f1cabc9d41058ba89662f5e06a10
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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