Trimethylsilyl iodide → HCID 178498215, compound

HRID 215827Notes

Reaction equation

HRID 215827 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[N:13][C:14]([O:17]C)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1.I[Si](C)(C)C>C(#N)C.O>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[N:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67297135HCID 67297135, compound

Product 1

HCID 178498215HCID 178498215, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(6-methoxy-pyridin-3-yloxy)-benzoic acid methyl ester (0.2 g, 0.8 mmol) in acetonitrile (6 ml) was added iodotrimethylsilane (0.346 g, 1.73 mmol) and the mixture was allowed to reflux for 1 h. The reaction mixture was diluted with water (8 ml) and extracted with chloroform. The extract was washed with 10% aqueous Na2S2O3 and water and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford 0.19 g (87%) of 4-(6-hydroxy-pyridin-3-yloxy)-benzoic acid methyl ester as yellowish crystals.

Workup

  1. temperatureto reflux for 1 h
  2. extractionextracted with chloroform
  3. washThe extract was washed with 10% aqueous Na2S2O3 and water
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ab67c8708d3049f9b1a1a935d8168fff
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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