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

HRID 1851097ノート

反応式

HRID 1851097 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 6386tert-Butanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-180f36689ade41aeb65c09a954826100
出典データセット
uspto-grants-2015_02
特許番号
US08957102B2

反応ノート

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