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Potassium Hydroxide → (2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoic acid

HRID 1850053
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1850053
[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([O:11]C)=[O:10])[CH:4]=[N:3]1.[OH-].[K+]>CO>[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])[CH:4]=[N:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 21936263methyl 3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoate

Produkt 1

HCID 1529858(2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoic acidAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(E)-methyl 3-(1-methyl-1H-pyrazol-4-yl)acrylate (0.24 g, 1.45 mmol) was dissolved in MeOH (10 mL). A 1M solution of KOH (5.8 mL) was added and the mixture was heated at 70° C. overnight. The reaction mixture was then evaporated under reduced pressure and water (10 mL) was added to the residue. This solution was carefully acidified to pH 4 with a 3M aqueous solution of HCl. The carboxylic acid precipitated and was extracted with ethyl acetate. The EtOAc layer was washed with water (2×10 mL) and brine (1×15 mL). It was dried over sodium sulfate, filtered and evaporated under vacuum to give (E)-3-(1-methyl-1H-pyrazol-4-yl)acrylic acid as a white solid (160 mg). ES+(M+H)+153

Aufarbeitung

  1. customThe reaction mixture was then evaporated under reduced pressure and water (10 mL)
  2. additionwas added to the residue
  3. customThe carboxylic acid precipitated
  4. extractionwas extracted with ethyl acetate
  5. washThe EtOAc layer was washed with water (2×10 mL) and brine (1×15 mL)
  6. dry with materialIt was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3665a68fb83a4f2da6c304c861425e85
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08957066B2

Notizen zur Reaktion

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