Ethanol → (3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl}-1H-pyrazol-5-yl)methanol

HRID 2110865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110865
[C:1]([C:5]1[CH:9]=[C:8]([C:10](OCC)=[O:11])[N:7]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][O:23][CH2:24][O:25][CH3:26])=[CH:18][CH:17]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.[Cl-].[NH4+]>O1CCCC1>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][OH:11])[N:7]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23157202ethyl 3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl}-1H-pyrazole-5-carboxylate

Produkt 1

HCID 23157325(3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl}-1H-pyrazol-5-yl)methanolAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl}-1H-pyrazole-5-carboxylate (1.95 g, 5.41 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (0.26 g, 5.5 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Ethanol (10 mL) and saturated aqueous ammonium chloride solution (1.0 mL) were added to the reaction mixture. The precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue subjected to silica gel chromatography (ethyl acetate:hexane=1:1) to give the title compound (1.45 g, yield 84%) as a colorless oil.

Aufarbeitung

  1. temperaturecooling
  2. filtrationThe precipitated insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5328a687685044b6a5af7e2691c756ca
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517910B2

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