1-(toluene-4-sulfonyl)-1H-pyrazole-3-carbaldehyde → 1-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propan-1-ol

HRID 559723

Reaktionsgleichung

Reaktionsgleichung von HRID 559723
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[N:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:18]([Mg]Cl)[CH3:19]>C1COCC1.[Cl-].N>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH:15]([OH:16])[CH2:18][CH3:19])=[N:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 592783701-(toluene-4-sulfonyl)-1H-pyrazole-3-carbaldehydeHCID 178461633HCID 178461633, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 20976574Ammonia chlorideLösungsmittel

Versuchsvorschrift

To a chilled (−40° C.) solution of 1-(toluene-4-sulfonyl)-1H-pyrazole-3-carbaldehyde (1.50 g, 5.99 mmol) in THF was added a 2 M solution of ethylmagnesium chloride (3.00 mL, 6.00 mmol) in THF. After 3 hours, the mixture was diluted with saturated aqueous ammonia chloride and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate and the concentrated in vacuo. The residue was purified by reversed-phase HPLC. 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-ol.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationthe concentrated in vacuo
  5. customThe residue was purified by reversed-phase HPLC
  6. concentrationthe solvent was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e8ebaa39f3474b879862f91bec058c25
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063065B2

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