Ethyl Acetate → Ethyl 2-methyl-1,3-oxazole-4-carboxylate

HRID 602821Notes

Reaction equation

HRID 602821 reaction equation
[CH2:1]([O:3][C:4]([C:6]([N:9]=[C:10]([O:12][CH2:13]C)[CH3:11])=C[O-])=[O:5])[CH3:2].[K+].CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:9]=[C:10]([CH3:11])[O:12][CH:13]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86600794Potassium 2-ethoxycarbonyl-2-(1-ethoxy-ethylideneamino)-ethenolate

Product 1

HCID 10402496Ethyl 2-methyl-1,3-oxazole-4-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

5 g (25 mmol) of potassium 2-ethoxycarbonyl-2-(1-ethoxy-ethylideneamino)-ethenolate were completely dissolved in 15 mL acetic acid at RT, and then the solution was heated to 110° C. overnight. After cooling down, 100 mL EtOAc were added and the solution is neutralized with saturated NaHCO3 solution. The organic phase was separated, dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel (heptane/EtOAc 1:2) yielded 1.74 g (45%) of 2-methyl-oxazole-4-carboxylic acid ethyl ester as an yellow oil, MS: 156 (MH+).

Workup

  1. temperatureAfter cooling down
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c04230959fd24adb8c67e3a051985410
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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