Sodium Sulfite → HCID 86605796, compound

HRID 2221833Notes

Reaction equation

HRID 2221833 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:39])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][O:20][C:21]3[C:25](/[CH:26]=[CH:27]/[S:28]([CH3:30])=[O:29])=[CH:24][N:23]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:22]=3)=[CH:15][C:14]=2[O:37][CH3:38])[N:10]=1.ClC1C=CC=C(C(OO)=[O:48])C=1.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:39])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][O:20][C:21]3[C:25](/[CH:26]=[CH:27]/[S:28]([CH3:30])(=[O:48])=[O:29])=[CH:24][N:23]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:22]=3)=[CH:15][C:14]=2[O:37][CH3:38])[N:10]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 69216387HCID 69216387, compound

Product 1

HCID 86605796HCID 86605796, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(2-furyl)-4-({2-methoxy-4-[({4-[(E)-2-(methylsulfinyl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]phenoxy}methyl)-5-methyl-1,3-oxazole (0.47 g) and tetrahydrofuran (30 mL) was added m-chloroperbenzoic acid (0.18 g) at room temperature, and the mixture was stirred at the same temperature for 1 hr. Saturated aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was stirred at room temperature for 10 min, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and 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, v/v) to give 2-(2-furyl)-4-({2-methoxy-4-[({4-[(E)-2-(methylsulfonyl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]phenoxy}methyl)-5-methyl-1,3-oxazole as colorless crystals (0.41 g, yield 85%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 152-153° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with ethyl acetate-hexane (1:1

Sources & evidence

ORD record
ord-5d0198ca60924395b99dbc7beee17f4c
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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