Water → Ethyl 5-methyl-1,3-oxazole-2-carboxylate

HRID 69089Notes

Reaction equation

HRID 69089 reaction equation
[CH2:1]([NH:5][C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([CH3:4])=O.O=P(Cl)(Cl)Cl.O>C1(C)C=CC=CC=1>[CH3:4][C:2]1[O:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5][CH:1]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 57348900Ethyl oxo[(2-oxopropyl)amino]acetate

Product 1

HCID 22099282Ethyl 5-methyl-1,3-oxazole-2-carboxylateYield 61.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of ethyl 2-(acetonylamino)-2-oxo-acetate (9.2 g, 53.12 mmol) in toluene (100.0 mL), is added POCl3 (4.95 mL, 53.12 mmol) and the reaction mixture is refluxed for 16 hours. The reaction mixture is cooled, added portionwise to water (100.0 mL) and stirred vigorously. The organic layer is washed with saturated NaHCO3 solution (2×50 mL), water (2×50 mL), dried over Na2SO4, and evaporated under reduced pressure. The crude material is purified by silica gel chromatography eluting with hexane:ethyl acetate (8.0:2.0) to give the title compound (5.1 g, 61.9%) as a yellow oil. ESI/MS m/z 156.2.1 (M+H)+.

Workup

  1. temperaturethe reaction mixture is refluxed for 16 hours
  2. temperatureThe reaction mixture is cooled
  3. washThe organic layer is washed with saturated NaHCO3 solution (2×50 mL), water (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude material is purified by silica gel chromatography
  7. washeluting with hexane:ethyl acetate (8.0:2.0)

Sources & evidence

ORD record
ord-eb3b587111da45c19727cb96ab7d371c
Source dataset
uspto-grants-2014_09
Patent number
US08822486B2

Reaction notes

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