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

HRID 1778196ノート

反応式

HRID 1778196 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-61f03395f4d543b88452051962bba683
出典データセット
uspto-grants-2016_02
特許番号
US09266891B2

反応ノート

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