Sodium Hydroxide → 2-Ethyloxazole-5-carboxylic acid

HRID 70901Notes

Reaction equation

HRID 70901 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-17da62ca61434fe7be8d80e287748b26
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

Loading…