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

HRID 2068826Notes

Reaction equation

HRID 2068826 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

HCID 141352365-Methyl-1-phenylpyrazole-3-carbaldehydeYield 81.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9d59da27d5a34a238938585f29a33a4e
Source dataset
uspto-grants-2012_10
Patent number
US08299072B2

Reaction notes

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