Aluminium lithium hydride → 1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde

HRID 2090936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090936
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[C:11]([C:13](OC)=[O:14])[C:10]([CH3:17])=[N:9]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[C:11]([CH:13]=[O:14])[C:10]([CH3:17])=[N:9]1

Komponenten

6

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 66777678HCID 66777678, Verbindung2×

Produkt 1

HCID 433815061-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehydeAusbeute 15,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution (20 mL) of methyl 1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carboxylate (2.0 g) synthesized in the above-mentioned (1) in tetrahydrofuran was added to an ice-cooled solution (20 mL) of lithium aluminum hydride (0.30 g) in tetrahydrofuran. The ice bath was removed, and the reaction mixture was stirred at room temperature for 1 hr. The mixture was ice-cooled again, and water (0.80 mL), 1N aqueous sodium hydroxide solution (4.0 mL) and water (0.80 mL) were successively added dropwise to quench the reaction. The residue was filtered through celite, and the filtrate was concentrated under reduced pressure to give a crude product (0.36 g) of 1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-methanol as a pale-yellow oil. This was dissolved in toluene (10 mL), manganese dioxide (2.0 g) was added, and the mixture was heated under reflux with a Dean-Stark trap for 1 hr. The reaction mixture was allowed to cool to room temperature, and manganese dioxide was collected by filtration. The solvent was evaporated under reduced pressure to give the title object compound (0.27 g, 15%) as a colorless solid.

Aufarbeitung

  1. customThe ice bath was removed
  2. temperaturecooled again
  3. additionwater (0.80 mL), 1N aqueous sodium hydroxide solution (4.0 mL) and water (0.80 mL) were successively added dropwise
  4. customto quench
  5. customthe reaction
  6. filtrationThe residue was filtered through celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customto give a crude product (0.36 g) of 1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-methanol as a pale-yellow oil
  9. temperaturethe mixture was heated
  10. temperatureunder reflux with a Dean-Stark trap for 1 hr
  11. temperatureto cool to room temperature
  12. filtrationmanganese dioxide was collected by filtration
  13. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-97bedd54db654e0483e48f9ed2e73b54
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436043B2

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