Hydrochloric Acid → HCID 22220967, compound

HRID 1794456Notes

Reaction equation

HRID 1794456 reaction equation
[C:1]([CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([O:22]C)(=[O:21])[CH:19]=[CH2:20].CC(C)([O-])C.[K+].Cl.[OH-].[Na+].C[N:34](C)C=O>CO>[C:11]1([C:10]2[C:9]([CH2:20][CH2:19][C:18]([OH:22])=[O:21])=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[O:8][N:34]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 6

HCID 313Hydrochloric Acid2×HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 8433DibenzoylmethaneHCID 14798Sodium HydroxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22220967HCID 22220967, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of dibenzoylmethane (4.48 g), methyl acrylate (1.8 ml), potassium t-butoxide (0.23 g) and N,N-dimethylformamide (40 ml) was stirred at room temperature overnight. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and a colorless oil was obtained from a fraction eluted with ethyl acetate-hexane (1:9, volume ratio). A mixture of the obtained colorless oil, hydroxylamine hydrochloride (1.00 g) and isopropyl alcohol (50 ml) was refluxed for 6 hr. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a colorless oil. A mixture of the obtained colorless oil, 2N sodium hydroxide (20 ml) and methanol (30 ml) was stirred at room temperature for 2 hr. The reaction mixture was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were filtrated to give 3-[3,5-diphenyl-4-isoxazolyl]propionic acid (1.91 g, yield 33%). The crystals were recrystallized from ethanol. melting point: 152–153° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customa colorless oil was obtained from a fraction
  6. washeluted with ethyl acetate-hexane (1:9, volume ratio)
  7. additionA mixture of the obtained colorless oil, hydroxylamine hydrochloride (1.00 g) and isopropyl alcohol (50 ml)
  8. temperaturewas refluxed for 6 hr
  9. additionThe reaction mixture was poured into dilute hydrochloric acid
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with saturated brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated
  14. customto give a colorless oil
  15. stirringwas stirred at room temperature for 2 hr
  16. extractionextracted with ethyl acetate
  17. washThe ethyl acetate layer was washed with saturated brine
  18. dry with materialdried (MgSO4)
  19. concentrationconcentrated
  20. filtrationThe obtained colorless crystals were filtrated

Sources & evidence

ORD record
ord-c26a5dc80ebc4e03afec54e1b55c9cec
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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