Dimethylformamide → (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid

HRID 30629

Reaktionsgleichung

Reaktionsgleichung von HRID 30629
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[CH:14]=O)=[CH:4][CH:3]=1.[H-].[Na+].C(OP([CH2:26][C:27]([O:29]CC)=[O:28])(OCC)=O)C.CN(C)C=O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 231574845-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carbaldehyde

Produkt 1

HCID 69208981(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carbaldehyde (350 mg), sodium hydride (60% in oil, 120 mg), ethyl diethylphosphonoacetate (673 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the precipitated solids were collected by filtration. After drying with airflow, the solids were dissolved in a mixed solvent of tetrahydrofuran (10 ml) and ethanol (10 ml). A 1N aqueous sodium hydroxide solution (5 ml) was added and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into a 10% aqueous citric acid solution and the precipitated solids were collected by filtration, washed with water and dried with airflow to give (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid (354 mg, 84%) as crystals. Recrystallization thereof from methanol-isopropyl ether gave colorless prism crystals. melting point: 212-213° C.

Aufarbeitung

  1. filtrationthe precipitated solids were collected by filtration
  2. customAfter drying with airflow
  3. dissolutionthe solids were dissolved in a mixed solvent of tetrahydrofuran (10 ml) and ethanol (10 ml)
  4. additionA 1N aqueous sodium hydroxide solution (5 ml) was added
  5. stirringthe mixture was stirred at room temperature for 2 hrs
  6. additionThe reaction mixture was poured into a 10% aqueous citric acid solution
  7. filtrationthe precipitated solids were collected by filtration
  8. washwashed with water
  9. customdried with airflow

Quellen und Nachweise

ORD-Eintrag
ord-cd79cd78a24d48dbb3bf376e220e8d48
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423159B2

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