Lithium Hydroxide → 1-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid

HRID 1011865

反応式

HRID 1011865 の反応式
C[O:2][C:3]([C:5]1[C:6]([CH2:27][CH3:28])=[N:7][N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH:13]=2)[C:9]=1[CH2:10][CH3:11])=[O:4].[OH-].[Li+]>C1COCC1.CO>[Cl:26][C:23]1[CH:24]=[CH:25][C:20](/[CH:19]=[CH:18]/[C:14]2[CH:13]=[C:12]([N:8]3[C:9]([CH2:10][CH3:11])=[C:5]([C:3]([OH:4])=[O:2])[C:6]([CH2:27][CH3:28])=[N:7]3)[CH:17]=[CH:16][CH:15]=2)=[CH:21][CH:22]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 673141011-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester

生成物 1

HCID 673139751-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid収率 98.6%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

A solution of 1.78 g (4.5 mmol) of 1-{3-[(E)-2-(4-chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester in 100 ml of THF/MeOH (1:1) was treated with 11.3 ml of lithium hydroxide solution (1 M in water) at RT and then stirred at reflux (boiling temperature=80° C.) for 60 hours. The reaction mixture was then cooled to RT and evaporated. The residue was partitioned between water and CH2Cl2, acidified with HCl (2N) to pH 1-2 and extracted twice with CH2Cl2. The organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 1.69 g of crude title compound as light yellow solid. MS: 379.2 ([M−H]−, 1 Cl).

後処理

  1. temperatureat reflux (boiling temperature=80° C.) for 60 hours
  2. customevaporated
  3. customThe residue was partitioned between water and CH2Cl2
  4. extractionextracted twice with CH2Cl2
  5. washThe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-c38d78e5671f407a918fe95029c07b2b
出典データセット
uspto-grants-2011_07
特許番号
US07977358B2

関連ノート

読み込み中…