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

HRID 1485027노트

반응식

HRID 1485027 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 (30.29 g; 321.80 mmol) was dissolved in DMA and K2CO3 (88.95 g; 643.60 mmol) was added portion wise. It was stirred for 10 minutes, then 5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (50.0 g; 214.53 mmol) was dropped to the reaction mixture and heated up to 140° C. for 16 hours. A 10% citric acid solution was added and extracted with DCM. The organic layer was washed with sodium bicarbonate and brine, then dried and purified through column chromatography.

후처리

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

출처 및 근거

ORD 기록
ord-70b426cd3fd9498b96b03a79c9a057ce
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422290B2

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