Dimethylformamide → ethyl {4-[4-({4-[({4-[(Z)-2-(1-ethyl-1H-imidazol-5-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}acetate

HRID 2222006Notes

Reaction equation

HRID 2222006 reaction equation
[CH:1]([C:3]1[C:4]([O:14][CH2:15][C:16]2[CH:42]=[CH:41][C:19]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:29]4[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][CH:30]=4)[O:25][C:26]=3[CH2:27]C)=[C:18]([O:43][CH3:44])[CH:17]=2)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1)=O.Cl.[Cl-].[CH2:47]([N:49]1[C:53]([CH2:54][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:52][N:51]=[CH:50]1)[CH3:48].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:47]([N:49]1[C:53](/[CH:54]=[CH:1]\[C:3]2[C:4]([O:14][CH2:15][C:16]3[CH:42]=[CH:41][C:19]([O:20][CH2:21][C:22]4[N:23]=[C:24]([C:29]5[CH:30]=[CH:31][C:32]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:33][CH:34]=5)[O:25][C:26]=4[CH3:27])=[C:18]([O:43][CH3:44])[CH:17]=3)=[N:5][N:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:7]=2)=[CH:52][N:51]=[CH:50]1)[CH3:48]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86605744[(1-ethyl-1H-imidazol-5-yl)methyl](triphenyl)phosphonium chloride hydrochlorideHCID 86605920ethyl (4-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl)-2-methoxyphenoxy)methyl]-5-ethyl-1,3-oxazol-2-yl}phenyl)acetate

Product 1

HCID 86605919ethyl {4-[4-({4-[({4-[(Z)-2-(1-ethyl-1H-imidazol-5-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}acetateYield 20.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl (4-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl)-2-methoxyphenoxy)methyl]-5-ethyl-1,3-oxazol-2-yl}phenyl)acetate (2.00 g), [(1-ethyl-1H-imidazol-5-yl)methyl](triphenyl)phosphonium chloride hydrochloride (2.29 g), anhydrous potassium carbonate (1.78 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 16 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (9:1 to 1:0, v/v) to give ethyl {4-[4-({4-[({4-[(Z)-2-(1-ethyl-1H-imidazol-5-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}acetate as colorless crystals (0.459 g, yield 20%). The crystals were recrystallized from tetrahydrofuran-hexane. melting point: 85-86° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (9:1 to 1:0

Sources & evidence

ORD record
ord-f9921329321c49358a02619290f56d8d
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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