Hydrochloric Acid → 3-(Benzyloxy)-1,2-oxazole-5-carboxylic acid

HRID 535015Notes

Reaction equation

HRID 535015 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([O:16]C)=[O:15])[O:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[O:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 5324203Methyl 3-(benzyloxy)isoxazole-5-carboxylate

Product 1

HCID 136269673-(Benzyloxy)-1,2-oxazole-5-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 3-(benzyloxy)isoxazole-5-carboxylate (1.68 g, 7.2 mmol) and lithium hydroxide monohydrate (0.839 g, 20 mmol) in tetrahydrofuran (20 mL) and water (20 mL) was stirred at 40° C. for 4 h. 1 M hydrochloric acid solution was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain a solid (1.58 g, 100%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52ea5e18ab6d4a7192204064e4d81827
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

Loading…