Triacetoxyperiodinane → 1-tosyl-1H-pyrazole-4-carbaldehyde

HRID 559731

Reaktionsgleichung

Reaktionsgleichung von HRID 559731
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[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>C1COCC1.C([O-])(O)=O.[Na+]>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[C:13]([CH:15]=[O:16])[CH:12]=[N:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 59278506[1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol

Produkt 1

HCID 577430311-tosyl-1H-pyrazole-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of [1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol (5.20 g, 20.61 mmol) in THF was added Dess-Martin periodinane (15.00 g, 35.37 mmol). After 3 hours, the mixture was diluted with saturated aqueous NaHCO3 and filtered through diatomaceous earth. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 20-50% ethyl acetate in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford 1-(toluene-4-sulfonyl)-1H-pyrazole-4-carbaldehyde.

Aufarbeitung

  1. filtrationfiltered through diatomaceous earth
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with a gradient of 20-50% ethyl acetate in heptane
  7. concentrationthe solvent was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-790e87c37cbb42d1ae92ecf6ea4f61b6
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063065B2

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