Sulfuric Acid → 1-[(4-Methoxy)phenyl]-5-(methoxycarbonyl)pyrazole-3-carboxylic acid

HRID 2186234ノート

反応式

HRID 2186234 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]([C:18]([O:20]C)=[O:19])=[N:10]2)=[CH:5][CH:4]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]([C:18]([OH:20])=[O:19])=[N:10]2)=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 11748281Dimethyl 1-[(4-methoxy)phenyl]pyrazole-3,5-dicarboxylate

生成物 1

HCID 542100671-[(4-Methoxy)phenyl]-5-(methoxycarbonyl)pyrazole-3-carboxylic acid収率 63.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of dimethyl 1-[(4-methoxy)phenyl]pyrazole-3,5-dicarboxylate (32.7 g, 110 mmol) in 50 mL of dioxane and 100 mL of water was added concentrated sulfuric acid (1.50 mL, 28.2 mmol). The resulting solution was stirred at 100° C. for 18 h and then cooled to room temperature. The reaction was made basic with potassium carbonate and then extracted with ether to remove unreacted diester. The aqueous layer was acidified with HCl and was extracted twice with ethyl acetate. The combined organics were washed with brine, dried (MgSO4) and concentrated to afford 19.2 g (63%) of the title compound along with 5.0 g (15%) of unreacted starting material. The title compound was used without further purification. LRMS (ES−): 274.9 (M−H)−.

後処理

  1. temperaturecooled to room temperature
  2. extractionextracted with ether
  3. customto remove unreacted diester
  4. extractionwas extracted twice with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-64613a276fd349f4911636a919800b02
出典データセット
uspto-grants-2002_06
特許番号
US06403620B1

反応ノート

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