Dimethylformamide → 2-(2-furyl)-4-({2-methoxy-4-[({1-methyl-4-[(Z)-2-(1,3-thiazol-4-yl)ethenyl]-1H-pyrazol-3-yl}oxy)methyl]phenoxy}methyl)-5-methyl-1,3-oxazole

HRID 2221864Notes

Reaction equation

HRID 2221864 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:31])=[C:9]([CH2:11][O:12][C:13]2[CH:28]=[CH:27][C:16]([CH2:17][O:18][C:19]3[C:23]([CH:24]=O)=[CH:22][N:21]([CH3:26])[N:20]=3)=[CH:15][C:14]=2[O:29][CH3:30])[N:10]=1.[Cl-].[S:33]1[CH:37]=[C:36]([CH2:38][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:35]=[CH:34]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:31])=[C:9]([CH2:11][O:12][C:13]2[CH:28]=[CH:27][C:16]([CH2:17][O:18][C:19]3[C:23](/[CH:24]=[CH:38]\[C:36]4[N:35]=[CH:34][S:33][CH:37]=4)=[CH:22][N:21]([CH3:26])[N:20]=3)=[CH:15][C:14]=2[O:29][CH3:30])[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 22175328Triphenyl(1,3-thiazol-4-ylmethyl)phosphonium chlorideHCID 866058183-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 692173132-(2-furyl)-4-({2-methoxy-4-[({1-methyl-4-[(Z)-2-(1,3-thiazol-4-yl)ethenyl]-1H-pyrazol-3-yl}oxy)methyl]phenoxy}methyl)-5-methyl-1,3-oxazoleYield 26.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-methyl-1H-pyrazole-4-carbaldehyde (0.50 g), [(1,3-thiazol-4-yl)methyl]triphenylphosphonium chloride (0.95 g), potassium carbonate (0.33 g) and N,N-dimethylformamide (20 mL) was stirred at room temperature for 15 hrs, and further stirred at 50° C. for 3 hrs. Water was poured into the reaction mixture, 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 (1:1 to 3:1, v/v) to give 2-(2-furyl)-4-({2-methoxy-4-[({1-methyl-4-[(Z)-2-(1,3-thiazol-4-yl)ethenyl]-1H-pyrazol-3-yl}oxy)methyl]phenoxy}methyl)-5-methyl-1,3-oxazole as colorless crystals (0.16 g, yield 26%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 97-98° C.

Workup

  1. stirringfurther stirred at 50° C. for 3 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with ethyl acetate-hexane (1:1 to 3:1

Sources & evidence

ORD record
ord-5fff97ed0f5c456e8c6defe8674863fd
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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