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

HRID 1011865

Reaktionsgleichung

Reaktionsgleichung von HRID 1011865
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 673139751-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acidAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c38d78e5671f407a918fe95029c07b2b
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977358B2

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