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

HRID 570280

반응식

HRID 570280 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-b21275651e444a088b9c9f9ffef2a057
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023846B2

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