Acetic Acid → HCID 22344564, compound

HRID 2299810Notes

Reaction equation

HRID 2299810 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:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[C:29](=O)[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].C(O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.C(O)C>[O:24]1[CH:28]=[CH:27][CH:26]=[C:25]1/[C:29](=[N:21]/[O:20][CH2:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:23][CH:22]=1)/[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 9990260HCID 9990260, compoundHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

Product 1

HCID 22344564HCID 22344564, compoundYield 24.1%

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-(2-furyl)-4-oxobutyrate (347 mg), acetic acid (0.276 ml), sodium acetate (264 mg) and ethanol (20 ml) was heated to reflux for 96 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 E-4-(2-furyl)-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]butyrate (190 mg, yield 24%) as a colorless oil from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 96 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-82f00223bc3040889d50eb26dd61eb0c
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

Loading…