Triacetoxyperiodinane → HCID 67053017, compound

HRID 2387333Notes

Reaction equation

HRID 2387333 reaction equation
[CH3:1][N:2]([CH3:24])[CH:3]=[N:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([CH3:23])([CH3:22])[CH2:15][CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])(=[O:7])=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:24][N:2]([CH3:1])[CH:3]=[N:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([CH3:22])([CH3:23])[CH2:15][C:16](=[O:21])[C:17]([F:18])([F:19])[F:20])(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67053009HCID 67053009, compound

Product 1

HCID 67053017HCID 67053017, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added N-[1-dimethylaminomethylidene]-2-(4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)benzenesulfonamide (367 mg, 1.00 mmol) in 25 mL of dry dichloromethane, followed by the addition of Dess-Martin periodinane (600 mg, 1.42 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with 50 mL of saturated aqueous sodium bicarbonate solution and extracted with 250 mL of ethyl acetate. The organic layer was separated, washed with 50 mL of brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Dichloromethane was added to the residue and the solid which did not dissolve in dichloromethane was filtered. The mother liquor was then concentrated in vacuo and the crude mixture was purified by flash chromatography. The column was eluted with 0-40% EtOAc/hexanes to afford 345 mg (95%) of N-[1-dimethylaminomethylidene]-2-(4,4,4-trifluoro-1,1-dimethyl-3-oxobutyl)benzenesulfonamide. MS (ES+) m/z 365 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with 50 mL of saturated aqueous sodium bicarbonate solution
  2. extractionextracted with 250 mL of ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with 50 mL of brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionDichloromethane was added to the residue
  9. dissolutionthe solid which did not dissolve in dichloromethane
  10. filtrationwas filtered
  11. concentrationThe mother liquor was then concentrated in vacuo
  12. customthe crude mixture was purified by flash chromatography
  13. washThe column was eluted with 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-1ac1627c876d4e49857f92a3593c294b
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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