Phosphorus oxychloride → Ethyl 5-tert-butyl-1,3-oxazole-2-carboxylate

HRID 460217Notes

Reaction equation

HRID 460217 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([NH:7][CH2:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=O)[CH3:2].P(Cl)(Cl)(Cl)=O>>[CH2:1]([O:3][C:4]([C:5]1[O:14][C:9]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:8][N:7]=1)=[O:15])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11241370Ethyl[(3,3-dimethyl-2-oxobutyl)amino](oxo)acetate

Product 1

HCID 11788834Ethyl 5-tert-butyl-1,3-oxazole-2-carboxylate

Conditions

Temperature
105 °C

Procedure

The mixture of N-(3,3-dimethyl-2-oxo-butyl)-oxalamic acid ethyl ester (0.79 g, 3.67 mmol) and phosphorus oxychloride (2.0 mL, 22.0 mmol) was stirred at 105° C. under N2 for 2 h, cooled to RT, quenched slowly with ice-water, extracted with EtOAc. The combined organic portions were washed with brine, dried with Na2SO4, removal of the solvents gave a dark brownish oil which was purified by flash column chromatography to yield the title compound. MS m/z: 197.9 (M+H). Calc'd for C10H15NO3-197.23

Workup

  1. temperaturecooled to RT
  2. customquenched slowly with ice-water
  3. extractionextracted with EtOAc
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried with Na2SO4, removal of the solvents
  6. customgave a dark brownish oil which
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-2aae935d68c54f09aef6d48d5a156b4d
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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