Hydrochloric Acid → 2-tert-Butyl-5-methyl-oxazole-4-carboxylic acid

HRID 1897560Notes

Reaction equation

HRID 1897560 reaction equation
[C:1]([C:5]1[O:6][C:7]([CH3:14])=[C:8]([C:10]([O:12]C)=[O:11])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>C1COCC1.O>[C:1]([C:5]1[O:6][C:7]([CH3:14])=[C:8]([C:10]([OH:12])=[O:11])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 576597452-tert-Butyl-5-methyl-oxazole-4-carboxylic acid methyl ester

Product 1

HCID 576597472-tert-Butyl-5-methyl-oxazole-4-carboxylic acidYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-tert-butyl-5-methyloxazole-4-carboxylate (44 mg, 0.22 mmol) and lithium hydroxide hydrate (47 mg, 1.1 mmol) in THF (1 mL) and water (1 mL) was stirred at room temperature for 19 hours. To the reaction was added 1 M HCl(aq) (1.1 mL, 1.1 mmol) and water, and the reaction was extracted with ethyl acetate. The combined extracts were washed with water, dried over sodium sulfate, and evaporated to give 2-tert-butyl-5-methyloxazole-4-carboxylic acid (40 mg, 98% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.61 (s, 3H), 1.38 (s, 9H) ppm.

Workup

  1. extractionthe reaction was extracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-ec4690cdb29c47bfbce1e1f7d3e71921
Source dataset
uspto-grants-2013_08
Patent number
US08519137B2

Reaction notes

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