Ethyl 4-methyl-2-(4-methylbenzoylamino)-3-oxopentanoate → Ethyl 5-isopropyl-2-p-tolyloxazole-4-carboxylate

HRID 253336Notes

Reaction equation

HRID 253336 reaction equation
[CH3:1][CH:2]([CH3:21])[C:3](=[O:20])[CH:4]([NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]>P(Cl)(Cl)(Cl)=O>[CH:2]([C:3]1[O:20][C:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[N:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:21])[CH3:1]

Participants

3

Reactant 1

HCID 57434497Ethyl 4-methyl-2-(4-methylbenzoylamino)-3-oxopentanoate

Product 1

HCID 57434498Ethyl 5-isopropyl-2-p-tolyloxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

13 g of ethyl 4-methyl-2-(4-methylbenzoylamino)-3-oxopentanoate in 80 ml of phosphorus oxychloride are heated to the boil under reflux for 2 h. The phosphorus oxychloride is removed under reduced pressure and the resulting residue is dissolved in 200 ml of dichloromethane, washed three times with saturated NaHCO3 solution and dried over MgSO4, and the solvent is then removed under reduced pressure. This gives 11 g of ethyl 5-isopropyl-2-p-tolyloxazole-4-carboxylate as a brownish solid. C16H19NO3 (273.33), MS (ESI)=292 (M+H+), Rf (n-heptane:ethyl acetate)=2:1)=0.43.

Workup

  1. temperatureunder reflux for 2 h
  2. customThe phosphorus oxychloride is removed under reduced pressure
  3. dissolutionthe resulting residue is dissolved in 200 ml of dichloromethane
  4. washwashed three times with saturated NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-ddf629c850484fd6b3c8aac86d7aac8d
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Reaction notes

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