Potassium Carbonate → Methyl 5-oxazolecarboxylate

HRID 659745Notes

Reaction equation

HRID 659745 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH:5]=[O:6])C.CC1C=CC(S([CH2:18][N+:19]#[C-:20])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][O:3][C:4]([C:5]1[O:6][CH:20]=[N:19][CH:18]=1)=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70211Ethyl oxoacetateHCID 161915Tosylmethyl isocyanide

Product 1

HCID 2724619Methyl 5-oxazolecarboxylateYield 621.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of glyoxylic acid ethyl ester (50% w/w in toluene) (4 mL, 2 mmol) and Tosmic (3.86 g, 2 mmol) in MeOH (60 mL) was added K2CO3 (5.6 g, 4 mmol) and the mixture was stirred at reflux for 7 h. The solvent was then evaporated and 100 mL of water was added. This solution was saturated with sodium chloride and extracted with diethyl ether. The organic layer was washed with brine, dried (MgSO4) filtered and concentrated to give 1.58 g (60%) of oxazole-5-carboxylic acid methyl ester as white solid. m.p.=35-50° C.

Workup

  1. temperatureat reflux for 7 h
  2. customThe solvent was then evaporated
  3. addition100 mL of water was added
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2d3271978b1341ef9bbb0c7cfbbd12a7
Source dataset
uspto-grants-2011_12
Patent number
US08080669B2

Reaction notes

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