Sodium Hydroxide → 2-Ethyloxazole-5-carboxylic acid
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
Product 1
Reagents, catalysts & solvents 1
Procedure
Next, 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, 3H) 2.89 (q, J=7.6 Hz, 2H) 5.15 (br. s., 1H) 7.69 (s, 1H)
Workup
- concentrationthe crude is concentrated under reduced pressure
- customto remove MeOH
- additionis diluted with EtOAc
- washThe organic layer is washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-cf5c6c91982d4e4eaa879bff0e5cb569
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263629B2
Reaction notes
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