Lithium Hydroxide → 1-(4-Methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylic acid

HRID 610130ノート

反応式

HRID 610130 の反応式
[OH-].[Li+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]([O:18]C)=[O:17])=[CH:14][C:13]([S:20][CH3:21])=[N:12]2)=[CH:7][CH:6]=1>CO>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]([S:20][CH3:21])=[N:12]2)=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 18177273methyl 1-(4-methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylate

生成物 1

HCID 181773011-(4-Methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylic acid収率 98.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of lithium hydroxide (4.5 mL, 1.0 M, 4.5 mmol) was added to a suspension of methyl 1-(4-methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylate (840 mg, 3.0 mmol) in MeOH (30 mL) and stirred at room temperatureerature for 21 hours. The resulting mixture was concentrated and partitioned between EtOAc and H2O. The organic layer was removed, and the aqueous layer was acidified with 1M HCl and extracted twice with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and evaporated to yield clean product (784 mg, 98%). 1H NMR (CDCl3): δ7.33 (d, 2H, J=8.4), 6.97 (s, 1H), 6.95 (d, 2H, J=8.4), 3.85 (s, 3H), 2.55 (s, 3H).

後処理

  1. concentrationThe resulting mixture was concentrated
  2. custompartitioned between EtOAc and H2O
  3. customThe organic layer was removed
  4. extractionextracted twice with EtOAc
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-ae3a38d5586a43b5b849de888d304f20
出典データセット
uspto-grants-1999_12
特許番号
US05998424

反応ノート

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