Citric Acid → 1-Methyl-5-phenoxy-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1778196노트

반응식

HRID 1778196 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH2:14]([O:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH3:25])[C:23]=1Br)=[O:18])[CH3:15].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(N(C)C)=O>[CH2:14]([O:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH3:25])[C:23]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:18])[CH3:15]

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 996PhenolHCID 11430Potassium CarbonateHCID 53302113Ethyl 5-Bromo-1-methyl-1H-pyrazole-4-carboxylate

생성물 1

HCID 867185501-Methyl-5-phenoxy-1H-pyrazole-4-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
140 °C

실험 절차

Phenol (30.3 g; 322 mmol) is dissolved in DMA and K2CO3 (88.9 g; 643 mmol) is added portion wise. It is stirred for 10 minutes, then 5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (50.0 g; 215 mmol) is dropped to the reaction mixture and heated up to 140° C. for 16 hours. A 10% citric acid solution is added and extracted with DCM. The organic layer is washed with sodium bicarbonate and brine, then dried and purified through column chromatography.

후처리

  1. extractionextracted with DCM
  2. washThe organic layer is washed with sodium bicarbonate and brine
  3. customdried
  4. custompurified through column chromatography

출처 및 근거

ORD 기록
ord-61f03395f4d543b88452051962bba683
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266891B2

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