Hexane → 5-Methyl-1-phenylpyrazole-3-carbaldehyde

HRID 2068826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068826
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1)=O)C.CC(C[AlH]CC(C)C)C.CCCCCC.C(OCC)(=O)C>C(Cl)Cl.O.CO>[CH:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1)=[O:3]

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 10900438Ethyl 5-methyl-1-phenyl-1H-pyrazole-3-carboxylate

Produkt 1

HCID 141352365-Methyl-1-phenylpyrazole-3-carbaldehydeAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Ethoxycarbonyl-1-phenyl-5-methylpyrazole (3.482 g, 15.12 mmol) was dissolved in 20 mL of purified methylene chloride, and then dropwisely added with DIBAL (45.36 mL, 45.36 mmol) at −78° C. and stirred. Termination of the reaction was confirmed by TLC (hexane:ethyl acetate=5:1). Upon completion of reaction, the reaction mixture was dropwisely added with methanol and water, and then extracted with methylene chloride. The resulting organic layer was dried with anhydrous magnesium sulfate and filtered, and the filtrate was concentrated and dried in vacuo to obtain the target compound, 3-formyl-5-methyl-1-phenylpyrazole.

Aufarbeitung

  1. customUpon completion of reaction
  2. extractionextracted with methylene chloride
  3. dry with materialThe resulting organic layer was dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9d59da27d5a34a238938585f29a33a4e
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299072B2

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