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

HRID 1748328Notes

Reaction equation

HRID 1748328 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>C1(C)C=CC=CC=1>[C:10]([C:9]1[O:14][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])=[N:7][CH:8]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

4

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-carboxylateYield 87.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of ethyl[(3,3-dimethyl-2-oxobutyl)amino](oxo)acetate (40 g, 162 mmol) in toluene (350 mL) is added phosphorous oxychloride (75 g, 488 mmol). The reaction mixture is heated at 120° C. for 14 h. Then the solvent is removed and the residue is diluted with ether. The ether layer is washed with saturated aqueous NaHCO3 solution, brine, dried (Na2SO4) and concentrated to afford the title compound (28 g, 87%).

Workup

  1. customThen the solvent is removed
  2. additionthe residue is diluted with ether
  3. washThe ether layer is washed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6e55317e44254676a0c61a3a5fb995f7
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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