Acetic Acid → HCID 22344652, compound

HRID 584496Notes

Reaction equation

HRID 584496 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.[CH3:24][C:25]([CH3:39])([C:31](=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.C(O)C>[CH3:39][C:25]([CH3:24])(/[C:31](=[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)/[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 251309Ethyl 2,2-dimethyl-3-oxo-3-phenylpropanoateHCID 517045Sodium AcetateHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

Product 1

HCID 22344652HCID 22344652, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (600 mg), ethyl 2,2-dimethyl-3-oxo-3-phenylpropionate (468 mg), acetic acid (0.331 ml), sodium acetate (317 mg) and ethanol (20 ml) was heated to reflux for 5 days, 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 Z-2,2-dimethyl-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-3-phenylpropionate (273 mg, yield 28%) as a colorless oil from an ethyl acetate-hexane (2:9, v/v)-eluted fraction.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 days
  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-660ecd3cec024c33a8755678872bb7bc
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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