Hydrochloric Acid → ethyl (2Z)-2-(3-benzoylphenyl)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]acetate

HRID 1070117Notes

Reaction equation

HRID 1070117 reaction equation
[H-].[Na+].[C:3]([C:11]1[CH:12]=[C:13](/[C:17](=[N:23]/[OH:24])/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:14]=[CH:15][CH:16]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:26][C:27]1[CH:46]=[CH:45][C:30]([O:31][CH2:32][C:33]2[N:34]=[C:35]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[O:36][C:37]=2[CH3:38])=[CH:29][CH:28]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[C:3]([C:11]1[CH:12]=[C:13](/[C:17](=[N:23]/[O:24][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:31][CH2:32][C:33]3[N:34]=[C:35]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[O:36][C:37]=3[CH3:38])=[CH:45][CH:46]=2)/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:14]=[CH:15][CH:16]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 87950554ethyl (2Z)-2-(3-benzoylphenyl)-2-hydroxyiminoacetate

Product 1

HCID 22344584ethyl (2Z)-2-(3-benzoylphenyl)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]acetateYield 41.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Sodium hydride (60% in oil, 399 mg) was added to a solution of ethyl Z-2-(3-benzoylphenyl)-2-hydroxyiminoacetate (2.47 g) and 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (2.61 g) in N,N-dimethylformamide (15 ml) at room temperature under nitrogen atmosphere and stirred for 1 hour. 1N hydrochloric acid (15 ml) was added, an aqueous saturated solution of sodium bicarbonate was added 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-(3-benzoylphenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetate (1.97 g, yield 41%) as a pale-yellow oil from an ethyl acetate-hexane (1:3, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b6ab7fcd4a694e1e9ffe32ca9aaf5770
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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