Lithium Hydroxide → 5-Chloro-1,2-oxazole-3-carboxylic acid

HRID 58521Notes

Reaction equation

HRID 58521 reaction equation
C(C1[CH:7]=[C:6]([Cl:8])[O:5][N:4]=1)C.[OH-:9].[Li+].[O:11]1[CH2:16][CH2:15]OCC1>>[Cl:8][C:6]1[O:5][N:4]=[C:15]([C:16]([OH:11])=[O:9])[CH:7]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 552649025-Chloro-3-ethyl-1,2-oxazole

Product 1

HCID 223114305-Chloro-1,2-oxazole-3-carboxylic acid

Procedure

Ethyl-5-chloroisoxazole (1.5 g; 8.54 mmol) was added to a mixture of lithium hydroxide (10 mL; 2M in water) and dioxane (10 mL). The reaction mixture was stirred vigorously at room temperature for 1 h and concentrated under reduced pressure. The crude material was reputed between ethyl acetate and HCl 1M; the phases were separated and the aqueous were extracted with ethyl acetate. The organic rejoined were dried, concentrated under reduced pressure and the crude material 1.2 g (95%) was used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe phases were separated
  3. extractionthe aqueous were extracted with ethyl acetate
  4. customThe organic rejoined were dried
  5. concentrationconcentrated under reduced pressure
  6. customthe crude material 1.2 g (95%) was used without further purification

Sources & evidence

ORD record
ord-6783c19611dd494fb97d8da5fc6b400e
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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