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

HRID 1011865

반응식

HRID 1011865 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c38d78e5671f407a918fe95029c07b2b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977358B2

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