Sodium periodate → HCID 58980662, compound

HRID 1787458Notes

Reaction equation

HRID 1787458 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 MeOH/THF (2:1, 15 mL). The mixture was stirred at 50° C. for 24 h, and then concentrated. The residue was diluted with Et2O and washed with water and saturated NaHCO3, dried over Na2SO4, filtered, and concentrated. Purification by silica-gel chromatography (0-50% EtOAc in CH2Cl2) provided 4-tert-butyl-1-methanesulfinyl-2-nitro-benzene (1.05 g, 91%) as a white solid.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with Et2O
  3. washwashed with water and saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica-gel chromatography (0-50% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-5b10c38e8a7e45b8b5154484cc9781cc
Source dataset
uspto-grants-2009_03
Patent number
US07511042B2

Reaction notes

Loading…