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

HRID 1918507Notes

Reaction equation

HRID 1918507 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

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 reparted 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-9e00ad74e5a342c1956f90931f991e4f
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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