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

HRID 2068826ノート

反応式

HRID 2068826 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 141352365-Methyl-1-phenylpyrazole-3-carbaldehyde収率 81.7%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9d59da27d5a34a238938585f29a33a4e
出典データセット
uspto-grants-2012_10
特許番号
US08299072B2

反応ノート

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