Potassium Carbonate → 5-(2-Pyridyl)oxazole

HRID 499452Notes

Reaction equation

HRID 499452 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].C1(C)C(S([CH2:18][N+:19]#[C-:20])(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[O:8]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:20][N:19]=[CH:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 142732-PyridinecarboxaldehydeHCID 53627694Toluenesulfonylmethyl isocyanide

Product 1

HCID 7371945-(2-Pyridyl)oxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Picolinaldehyde (2.5 g, 23 mmol) and toluenesulfonylmethyl isocyanide (5.3 g, 27 mmol) were dissolved in methanol (30 ml), and potassium carbonate (3.5 g, 25 mmol) was added thereto. The mixture was refluxed for 30 minutes. The solvent was evaporated, and ethyl acetate and water were added to the residue. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (2:3, v/v) were collected and concentrated to give the titled compound.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. customThe solvent was evaporated
  3. additionethyl acetate and water were added to the residue
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. washThe fractions eluted with hexane-ethyl acetate (2:3
  8. customv/v) were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2770995d5ba54c48be3092071237c900
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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