Sodium Hydroxide → 2-Ethyloxazole-5-carboxylic acid

HRID 881868Notes

Reaction equation

HRID 881868 reaction equation
[CH2:1]([C:3]1[O:4][C:5]([C:8]([O-:10])=[O:9])=[CH:6][N:7]=1)[CH3:2].[OH-].[Na+]>CO>[CH2:1]([C:3]1[O:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 534303822-Ethyloxazole-5-carboxylate

Product 1

HCID 212849102-Ethyloxazole-5-carboxylic acidYield 61.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-ethyloxazole-5-carboxylate (470 mg, 2.81 mmol) in MeOH (10 mL) is added 1N NaOH (6 mL, 6 mmol). After stirring at room temperature for 18 hours, the crude is concentrated under reduced pressure to remove MeOH and is diluted with EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 2-ethyloxazole-5-carboxylic acid (244 mg). 1H NMR (400 MHz, CD3OD) δ ppm 1.36 (t, J=7.7 Hz, 3 H) 2.89 (q, J=7.6 Hz, 2 H) 5.15 (br. s., 1 H) 7.69 (s, 1 H)

Workup

  1. concentrationthe crude is concentrated under reduced pressure
  2. customto remove MeOH
  3. additionis diluted with EtOAc
  4. washThe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aea15efe661342e0bac9bea836c3e657
Source dataset
uspto-grants-2015_03
Patent number
US08993631B2

Reaction notes

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