Ethyl 2-benzoylamino-3-oxobutanoate → Ethyl 5-methyl-2-phenyl-1,3-oxazole-4-carboxylate

HRID 453290Notes

Reaction equation

HRID 453290 reaction equation
[C:1]([NH:9][CH:10]([C:16](=[O:18])[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[CH3:17][C:16]1[O:18][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

3

Reactant 1

HCID 11425196Ethyl 2-benzoylamino-3-oxobutanoate

Product 1

HCID 3231335Ethyl 5-methyl-2-phenyl-1,3-oxazole-4-carboxylateYield 91.5%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of ethyl 2-benzamido-3-oxobutanoate (13.0 g, 0.052 mol) in phosphorus oxychloride (100 mL) was heated under reflux for 1.5 h, then cooled and concentrated under reduced pressure to a brown syrup which was dissolved in dichloromethane (250 mL). The solution was washed with water, saturated Na2CO3 and brine successively, then dried over anhydrous Na2SO4 and concentrated to give ethyl 5-methyl-2-phenyloxazole-4-carboxylate as a brown oil (11.0 g, 91% yield).

Workup

  1. temperatureunder reflux for 1.5 h
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure to a brown syrup which
  4. dissolutionwas dissolved in dichloromethane (250 mL)
  5. washThe solution was washed with water, saturated Na2CO3 and brine successively
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6631d2d4fda64b2ea004584aa7418ca4
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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