Aluminium lithium hydride → 2-Methyl-6-(trifluoromethyl)nicotinaldehyde

HRID 2265988

Reaktionsgleichung

Reaktionsgleichung von HRID 2265988
CON(C)[C:4]([C:6]1[C:7]([CH3:16])=[N:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:16][C:7]1[C:6]([CH:4]=[O:5])=[CH:11][CH:10]=[C:9]([C:12]([F:14])([F:13])[F:15])[N:8]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 86625530N-methoxy-N-methyl-2-methyl-6-trifluoromethyl-3-pyridinecarboxamide

Produkt 1

HCID 288753222-Methyl-6-(trifluoromethyl)nicotinaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a cooled (−78° C.) solution of N-methoxy-N-methyl-2-methyl-6-trifluoromethyl-3-pyridinecarboxamide (615 mg, 2.48 mmol) in THF (10 mL) was added lithium aluminum hydride (LAH, 1 N/THF, 1.23 mL). The mixture was stirred for 15 minutes, and then warmed to −10° C. After additional stirring for 30 minutes, the mixture was quenched with saturated potassium hydrogen sulfate solution (1 mL) and extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 2-methyl-6-trifluoromethyl-3-pyridinecarboxaldehyde quantitatively as oil. The crude product was used directly in the following reaction.

Aufarbeitung

  1. stirringAfter additional stirring for 30 minutes
  2. customthe mixture was quenched with saturated potassium hydrogen sulfate solution (1 mL)
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-adf0009457f64c29bc936bb352070a78
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858621B2

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