Tetrahydrofuran → HCID 66726067, compound

HRID 1042093Notes

Reaction equation

HRID 1042093 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 (trade mark) (42.0 g) was added under ice-cooling, and the mixture was stirred at room temperature for 4 hr. The reaction solution was filtered to remove a white solid, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted 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 diethyl ether-hexane mixed solvent to give the title compound (11.0 g, yield 98%) as pale-yellow crystals.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. filtrationThe reaction solution was filtered
  4. customto remove a white solid
  5. concentrationthe filtrate was concentrated
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted 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 diethyl ether-hexane mixed solvent

Sources & evidence

ORD record
ord-e07e0ab906d84d4ca35cd980a8eebb53
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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