Methyl iodide → 6-Methoxythieno[3,2-b]pyridine

HRID 569072Notes

Reaction equation

HRID 569072 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[S:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:13]I>CS(C)=O>[CH3:13][O:1][C:2]1[CH:3]=[C:4]2[S:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20148567Thieno[3,2-b]pyridin-6-ol

Product 1

HCID 201485826-Methoxythieno[3,2-b]pyridineYield 78.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-hydroxythieno[3,2-b]pyridine (2.45 g, 16.2 mmol) in dry dimethylsulfoxide (15 ml), under a nitrogen atmosphere, was added 60% sodium hydride in mineral oil (0.75 g, 19 mmol) and let stir at room temperature for 1 hour. Methyl iodide (1.25 ml, 21 mmol) was added to this solution and it was stirred for an additional two hours. The solution was poured into ice/water and extracted with diethyl ether, washed with water, dried over anhydrous sodium sulfate, filtered and carefully evaporated to give an oily product (2.1 g, 78% yield) which was used as is.

Workup

  1. stirringwas stirred for an additional two hours
  2. extractionextracted with diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customcarefully evaporated

Sources & evidence

ORD record
ord-5e4ad5e54b854f339997a2ef5d46f549
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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