2-Methyl-2-butene → 1,2-dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid

HRID 1851097노트

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HRID 1851097 반응식
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([CH:13]=[O:14])[C:4](=[O:15])[N:3]1[CH3:16].CC(=CC)C.Cl([O-])=[O:23].[Na+].P([O-])([O-])[O-].[K+].[K+].[K+]>C(O)(C)(C)C.O>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([C:13]([OH:23])=[O:14])[C:4](=[O:15])[N:3]1[CH3:16]

참가 물질

7

반응물 4

HCID 105532-Methyl-2-buteneHCID 9837043phosphorous acid, tripotassium saltHCID 23668197Sodium ChloriteHCID 583683381,2-dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde

생성물 1

HCID 583683541,2-dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid수율 35%

시약·촉매·용매 2

HCID 962Water용매3회HCID 6386tert-Butanol용매

실험 절차

1,2-Dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde was dissolved in t-butyl alcohol (23.5 mL) and 2-methyl-2-butene (8.3 mL, 78.5 mmol) was added at 0° C. After adding an aqueous solution of sodium chlorite (80% tech, 0.95 g, 8.7 mmol) in water (10 mL) and a suspension of potassium phosphite monobasic (3.44 g, 25.3 mmol) in water (23.5 mL) to the resulting reaction mixture, the mixture was stirred at room temperature for 10 hours. After adding water to the stirred reaction mixture, the aqueous layer was extracted with ethyl acetate, dichloromethane and 10:1 dichloromethane/methanol. The organic layer was collected, dried with sodium sulfate, and then filtered. The filtrate was concentrated. The resulting residue was washed with a small volume of ethyl acetate to give the target compound as a white solid (350 mg, 1.5 mmol, 35% yield).

후처리

  1. customto the resulting reaction mixture
  2. customto the stirred reaction mixture
  3. extractionthe aqueous layer was extracted with ethyl acetate, dichloromethane and 10:1 dichloromethane/methanol
  4. customThe organic layer was collected
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. washThe resulting residue was washed with a small volume of ethyl acetate

출처 및 근거

ORD 기록
ord-180f36689ade41aeb65c09a954826100
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957102B2

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