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

HRID 2068826노트

반응식

HRID 2068826 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9d59da27d5a34a238938585f29a33a4e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299072B2

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