Water → 5-Methoxy-2-methylpyridine

HRID 2370866Notes

Reaction equation

HRID 2370866 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:11]I.O>CS(C)=O.CCOCC>[CH3:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[N:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydride

Product 1

HCID 133587775-Methoxy-2-methylpyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 60% NaH (in mineral oil) (18.27 g, 0.458 mol, Aldrich, India) in DMSO (66 mL, Spectrochem., India) at 0° C., was added 6-methylpyridin-3-ol (25.0 g, 0.229 mol) dissolved in DMSO (100 mL) drop wise over a period of 15 min. After complete addition, the reaction mixture was stirred at 0° C. for 40 min. Methyl iodide (29.5 mL, 0.458 mol, Spectrochem, India) was added and the reaction mixture was stirred at rt for 2 h. The reaction with water and Et2O (1:1, 200 mL). The organic layer was separated and aqueous layer was back extracted with Et2O (75 mL×3). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give the title compound as a dark brown gummy oil. 1H NMR (400 MHz, CDCl3) δ ppm 8.19 (d, J=2.8 Hz, 1H), 7.12-7.05 (m, 2H), 3.83 (s, 3H), 2.49 (s, 3H). MS (ESI, positive ion) m/z: 124.0 (M+H).

Workup

  1. additionAfter complete addition
  2. stirringthe reaction mixture was stirred at rt for 2 h
  3. customThe organic layer was separated
  4. extractionaqueous layer was back extracted with Et2O (75 mL×3)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-695548adc2da4e75856db561c990ed17
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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