Acetic Acid → methyl (6E)-2,2-dimethyl-6-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-6-phenylhexanoate

HRID 2299879Notes

Reaction equation

HRID 2299879 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]([CH3:41])([CH2:30][CH2:31][CH2:32][C:33](=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:26]([O:28][CH3:29])=[O:27].C(O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.CO>[CH3:24][C:25]([CH3:41])([CH2:30][CH2:31][CH2:32]/[C:33](=[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:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:26]([O:28][CH3:29])=[O:27]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 11043092Methyl 2,2-dimethyl-6-oxo-6-phenylhexanoateHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

Product 1

HCID 11145964methyl (6E)-2,2-dimethyl-6-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-6-phenylhexanoateYield 47%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (467 mg), methyl 2,2-dimethyl-6-oxo-6-phenylhexanoate (340 mg), acetic acid (0.259 ml), sodium acetate (248 mg) and methanol (15 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 methyl E-2,2-dimethyl-6-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-6-phenylhexanoate (348 mg, yield 47%) as a colorless oil from an ethyl acetate-hexane (1:5, 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-e4bb02cb58c64a939679aae1e21fb782
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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