Sodium periodate → HCID 58980662, compound

HRID 735791Notes

Reaction equation

HRID 735791 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=1)([CH3:10])([CH3:9])[CH3:8]>O.CO.C1COCC1>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:18])=[O:2])=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 58980345HCID 58980345, compound

Product 1

HCID 58980662HCID 58980662, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Sodium periodate (1.23 g, 5.76 mmol) in water (2.0 mL) was added to a solution of the above thioether (1.08 g, 4.80 mmol) in methanol/THF (2:1, 15 mL). The mixture was stirred at 50° C. for 24 h, then the solvent was concentrated in vacuo. The residue was diluted with diethyl ether and washed with water and saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the crude product by silica-gel chromatography (methylene chloride—50% ethyl acetate in methylene chloride) provided 4-tert-butyl-1-methanesulfinyl-2-nitro-benzene (1.05 g, 91%) as a white solid.

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. additionThe residue was diluted with diethyl ether
  3. washwashed with water and saturated aqueous NaHCO3
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude product by silica-gel chromatography (methylene chloride—50% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-ffdfe1da4434455eabd861f30ca73fd7
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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