Trimethylsilyl iodide → HCID 178468932, compound

HRID 215830Notes

Reaction equation

HRID 215830 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:13]=[N:14][C:15]([O:18]C)=[CH:16][CH:17]=2)[CH:6]=1)[CH3:2].I[Si](C)(C)C>C(#N)C.O>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:13]=[N:14][C:15]([OH:18])=[CH:16][CH:17]=2)[CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 672971443-(6-Methoxy-pyridin-3-yloxy)-benzoic acid ethyl ester

Product 1

HCID 178468932HCID 178468932, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(6-methoxy-pyridin-3-yloxy)-benzoic acid ethyl ester (0.5 g, 1.83 mmol) in acetonitrile (8 ml) and iodotrimethylsilane (0.439 g, 2.2 mmol) was refluxed for 1 h, the mixture was diluted with water (8 ml) and extracted with chloroform. The extract was washed with 10% of aqueous Na2S2O3, water, dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to afford 0.327 g (69%) of 3-(6-hydroxy-pyridin-3-yloxy)-benzoic acid ethyl ester as colorless powder.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with 10% of aqueous Na2S2O3, water
  3. dry with materialdried over anhydrous Na2SO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7966cc72d6c1417f9aee8da87b3704aa
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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