Acetic Acid → HCID 53700113, compound

HRID 1070141Notes

Reaction equation

HRID 1070141 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1.O=[C:25]([C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1)[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20][N:21]=[C:25]([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 10943675Ethyl 4-oxo-4-(4-pyridyl)butyrateHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

Product 1

HCID 53700113HCID 53700113, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (500 mg), ethyl 4-oxo-4-(4-pyridyl)butyrate (367 mg), acetic acid (0.276 ml), sodium acetate (264 mg) and ethanol (20 ml) was heated to reflux for 15 hours, the mixture was cooled to room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl 4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-(4-pyridyl)butyrate (740 mg, yield 92%) as a colorless oil from an ethyl acetate-hexane (3:2, v/v)-eluted fraction.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 15 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0ebeb7023c35493ba08388326f3cd66d
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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