Potassium Carbonate → HCID 136463821, compound

HRID 862101Notes

Reaction equation

HRID 862101 reaction equation
[C:1]([O:5][N:6]=[C:7]([C:21]1[C:26]([OH:27])=[CH:25][CH:24]=[CH:23][N:22]=1)[C:8]1[CH:13]=[C:12]([C:14]#[C:15][Si](C)(C)C)[CH:11]=[CH:10][C:9]=1[OH:20])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5]/[N:6]=[C:7](\[C:21]1[C:26]([OH:27])=[CH:25][CH:24]=[CH:23][N:22]=1)/[C:8]1[CH:13]=[C:12]([C:14]#[CH:15])[CH:11]=[CH:10][C:9]=1[OH:20])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 136395983HCID 136395983, compound

Product 1

HCID 136463821HCID 136463821, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (50 ml) was dissolved 2-[2-hydroxy-5-(2-trimethylsilylethynyl)benzoyl]-3-hydroxypyridine O-t-butyl oxime (0.70 g). To the solution was added potassium carbonate (0.1 g) at room temperature, followed by heating for 3 hours under reflux. The reaction mixture was cooled by aeration, then the solvent was distilled off. To the residue were added chloroform and water for extraction. The organic layer was dried (anhydrous magnesium sulfate), then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give (Z)-2-(5-ethynyl-2-hydroxybenzoyl)-3-hydroxypyridine O-t-butyloxime (0.21 g) (Compound 115).

Workup

  1. temperatureby heating for 3 hours
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was cooled by aeration
  4. distillationthe solvent was distilled off
  5. additionTo the residue were added chloroform and water
  6. extractionfor extraction
  7. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e5c750e8e7c64867accb4d915d8a86ab
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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