Water → [5-tert-Butyl-1-(4-methanesulfonyl-phenyl)-1H-pyrazol-3-yl]-methanol

HRID 508614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508614
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:8]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[N:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.O>C1COCC1>[C:11]([C:9]1[N:8]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:17][CH:16]=2)[N:7]=[C:6]([CH2:4][OH:3])[CH:10]=1)([CH3:14])([CH3:12])[CH3:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 596493465-tert-Butyl-1-(4-methanesulfonyl-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester

Produkt 1

HCID 67992518[5-tert-Butyl-1-(4-methanesulfonyl-phenyl)-1H-pyrazol-3-yl]-methanolAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of compound 3h (0.8 g, 2.28 mmol) in 25 mL of THF was added LiAlH4 (0.14 g, 3.65 mmol). The reaction mixture was stirred for 6 hours at room temperature. EtOAc (50 mL) and water (50 mL) were added successively. The solvent was removed in vacuo and the resulting solid was filtered. The crude product was purified by column chromatography (EtOAc/Hexanes=7/3) to give the titled compound (0.56 g, 80% yield) as a white solid. mp 143.0-146.5° C. 1H NMR (300 MHz, DMSO-d6): δ 8.06 (d, J=8 Hz, 2H), 7.68 (d, J=8 Hz, 2H), 6.26 (s, 1H), 5.10 (t, J=6 Hz, 1H), 4.39 (d, J=6 Hz, 2H), 3.32 (s, 3H), 1.14 (s, 9H).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. filtrationthe resulting solid was filtered
  3. customThe crude product was purified by column chromatography (EtOAc/Hexanes=7/3)

Quellen und Nachweise

ORD-Eintrag
ord-353e906e78b3443abb071195ef27aa62
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096532B2

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