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

HRID 1361229

Reaktionsgleichung

Reaktionsgleichung von HRID 1361229
[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-2c382169f5a04a7c9b5b1efa9a5b1be3
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879873B2

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