Ammonium Chloride → (1-benzyl-1H-pyrazol-4-yl)methanol

HRID 269799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269799
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1>[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 15237993ethyl 1-benzyl-1H-pyrazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 16769828(1-benzyl-1H-pyrazol-4-yl)methanolAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The ethyl 1-benzylpyrazole-4-carboxylate (5 g, 21.7 mmol) prepared in Example 9 was dissolved in THF (40 ml) and cooled to 0 degrees under inert atmosphere. Lithium Aluminum Hydride (1M in THF, 21.7 ml) was added dropwise. After complete addition, the solution was allowed to warm to room temperature and stirred for 2 hours. Saturated ammonium chloride solution was added slowly until gas evolution ceased. All solvent was removed in vacuo. To the residue was added 100 ml water and 250 ml ethyl acetate and placed in a separatory funnel. The organic layer was washed with water and concentrated to yield [1-benzylpyrazol-4-yl]methan-1-ol (3.8 g, HNMR)

Aufarbeitung

  1. temperaturecooled to 0 degrees under inert atmosphere
  2. additionAfter complete addition
  3. customAll solvent was removed in vacuo
  4. additionTo the residue was added 100 ml water and 250 ml ethyl acetate
  5. customplaced in a separatory funnel
  6. washThe organic layer was washed with water
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-76d1ef395f494f28b99f7bff601df27c
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449473B2

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