Sodium Hydroxide → 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylic acid

HRID 570280

反応式

HRID 570280 の反応式
[C:1]([C:5]1[C:9]([Cl:10])=[C:8]([C:11]([O:13]CC)=[O:12])[N:7]([CH3:16])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([C:5]1[C:9]([Cl:10])=[C:8]([C:11]([OH:13])=[O:12])[N:7]([CH3:16])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 67412028ethyl 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylate

生成物 1

HCID 584254493-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A 12-L, four neck round bottom flask equipped with overhead air stirrer, positive pressure nitrogen inlet, thermocouple, and addition funnel was charged with ethyl 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylate (282 g, 1.15 mol) and EtOH (4.3 L). 3M NaOH (960 mL, 2.87 mol) was added in one portion and the resulting slurry began to clarify immediately. The resulting mixture was stirred at room temperature for 2 h and yielded a turbid solution. The turbid solution was evaporated and the resulting aqueous slurry was diluted with H2O (2 L). The basic solution was acidified to pH˜2 using concentrated HCl. The aqueous layer was extracted with dichloromethane (2×800 mL), dried over MgSO4, filtered, and evaporated to yield 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylic acid as an off-white solid. 1H NMR (CHLOROFORM-d) δ: 4.11 (s, 3H), 1.41 (s, 9H)

後処理

  1. additionthermocouple, and addition funnel
  2. customyielded a turbid solution
  3. customThe turbid solution was evaporated
  4. additionthe resulting aqueous slurry was diluted with H2O (2 L)
  5. extractionThe aqueous layer was extracted with dichloromethane (2×800 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-b21275651e444a088b9c9f9ffef2a057
出典データセット
uspto-grants-2015_05
特許番号
US09023846B2

関連ノート

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