Dimethylformamide → methyl (4E)-4-phenyl-4-[[4-[(5-phenyl-1,2-oxazol-3-yl)methoxy]phenyl]methoxyimino]butanoate

HRID 1070157Notes

Reaction equation

HRID 1070157 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1.O[CH:15]([C:30]1[CH:35]=[CH:34][CH:33]=CC=1)[CH2:16][C:17](=[N:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]([O-])=O.C(=O)([O-])[O-:37].[K+].[K+].CN(C)C=O.[C:47]([O:50][CH2:51]C)(=[O:49])[CH3:48].CCCCCC>O>[C:16]1(/[C:17](=[N:21]/[O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:37][CH2:2][C:3]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[O:5][N:4]=3)=[CH:28][CH:29]=2)/[CH2:18][CH2:48][C:47]([O:50][CH3:51])=[O:49])[CH:15]=[CH:30][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14847693-(Chloromethyl)-5-phenyl-1,2-oxazoleHCID 21226206Ethyl acetate hexaneHCID 1317227234-Hydroxybenzyloxyimino-4-phenylbutyrate

Product 1

HCID 11730378methyl (4E)-4-phenyl-4-[[4-[(5-phenyl-1,2-oxazol-3-yl)methoxy]phenyl]methoxyimino]butanoateYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(chloromethyl)-5-phenylisoxazole (340 mg), methyl E-4-(4-hydroxybenzyloxyimino-4-phenylbutyrate (500 mg), potassium carbonate (442 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 72 hours. 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-4-phenyl-4-[4-(5-phenyl-3-isoxazolylmethoxy)benzyloxyimino]butyrate (472 mg, yield 63%) as a colorless oil from an ethyl acetate-hexane (2:9, 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-32b3656aa86744a79e99edc5c2c75771
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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