Ethyl 2-vinyloxazole-5-carboxylate → 5-Oxazolecarboxylic acid, 2-ethyl-, ethyl ester

HRID 70900Notes

Reaction equation

HRID 70900 reaction equation
[CH:1]([C:3]1[O:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:7]=1)=[CH2:2].[H][H]>CO.[Pd]>[CH2:1]([C:3]1[O:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 59607716Ethyl 2-vinyloxazole-5-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 596076505-Oxazolecarboxylic acid, 2-ethyl-, ethyl esterYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-vinyloxazole-5-carboxylate (470 mg, 2.81 mmol) in MeOH (7 mL) is added 10% wt. Pd/C (100 mg, 0.094 mmol) at room temperature. After stirring at room temperature under a balloon of hydrogen for 1 hour, the crude is filtered to remove Pd/C. The filtrate is collected and concentrated to give ethyl 2-ethyloxazole-5-carboxylate (470 mg). HPLC retention time=1.09 minutes (condition A); MS (m+1)=170.3; 1H NMR (400 MHz, CD3OD) δ ppm 1.35 (t, J=7.6 Hz, 3 H) 1.36 (t, J=7.2 Hz, 3 H) 2.87 (q, J=7.7 Hz, 2 H) 4.35 (q, J=7.2 Hz, 2 H) 7.71 (s, 1 H)

Workup

  1. filtrationthe crude is filtered
  2. customto remove Pd/C
  3. customThe filtrate is collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dcc5c7355204493c970f9194e916c407
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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