Tetrahydrofuran → HCID 66726067, compound

HRID 1188871Notes

Reaction equation

HRID 1188871 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19](SC)=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:24]([O-:26])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[O:28][S:29]([O-:31])=O.[K+].O1CCC[CH2:34]1>CO.O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[CH:18][C:19]([S:29]([CH3:34])(=[O:31])=[O:28])=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]=1[N+:24]([O-:26])=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 66726142HCID 66726142, compound

Product 1

HCID 66726067HCID 66726067, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(Benzyloxy)-4-[4-(methylthio)phenoxy]-1-nitrobenzene (10.3 g) was dissolved in a mixed solvent of tetrahydrofuran (200 mL)-methanol (100 mL)-water (50 mL), OXONE (42.0 g) was added under ice-cooling, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was filtered to remove a white solid, and the filtrate was concentrated. Water was added to the residue, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained solid was washed with a mixed solvent of diethyl ether-hexane to give the title compound (11.0 g, yield 98%) as pale-yellow crystals. melting point 142-143° C.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. filtrationThe reaction mixture was filtered
  4. customto remove a white solid
  5. concentrationthe filtrate was concentrated
  6. additionWater was added to the residue
  7. extractionthe mixture was subjected to extraction with ethyl acetate
  8. washThe organic layer was washed successively with water and saturated brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. washThe obtained solid was washed with a mixed solvent of diethyl ether-hexane

Sources & evidence

ORD record
ord-605beba6fe7f418391d67ac573401d1c
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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