Triacetoxyperiodinane → HCID 59278091, compound

HRID 1361222

Reaction equation

HRID 1361222 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH:15]([OH:18])[CH2:16][CH3:17])=[N:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]1([CH3:19])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16][CH3:17])=[N:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 592783481-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propan-1-ol

Product 1

HCID 59278091HCID 59278091, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propan-1-ol (2.20 g, 7.85 mmol) in CH2Cl2 was added the Des s-Martin periodinane (4.24 g, 10.00 mmol). After 12 hours, the reaction was quenched with saturated aqueous sodium bicarbonate and filtered through diatomaceous earth and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 30% EtOAc in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford 1-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propan-1-one.

Workup

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate
  2. filtrationfiltered through diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 30% EtOAc in heptane
  6. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-73c1a6c8e0c948a4b161c0dad504ab5d
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Linked notes

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