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Sodium Hydroxide → 4-(1,4-dimethyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylic acid

HRID 1845584
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1845584
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:13]([O:15]C)=[O:14])[S:10][C:11]=2[CH3:12])=[C:5]([CH3:17])[CH:4]=[N:3]1.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:13]([OH:15])=[O:14])[S:10][C:11]=2[CH3:12])=[C:5]([CH3:17])[CH:4]=[N:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 57826452methyl 4-(1,4-dimethyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylate

Produkt 1

HCID 578266574-(1,4-dimethyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylic acidAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a 100 mL round-bottomed flask was added methyl 4-(1,4-dimethyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylate (1.31 g, 5.23 mmol) in Tetrahydrofuran (THF) (25 mL). 6N NaOH (30 mL, 180 mmol) was added slowly and the reaction stirred at 70° C. overnight. The reaction was cooled to room temperature, partitioned between CHCl3 and H2O and the pH of the aqueous layer adjusted to pH 3 by the addition of 6N HCl. The layers were separated, the organic layer was dried with Na2SO4 and the solvent was removed affording the title compound (1.3 g, 5.5 mmol, quant.) which was used without further purification: LC-MS (ES) m/z=237 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. custompartitioned between CHCl3 and H2O
  3. additionthe pH of the aqueous layer adjusted to pH 3 by the addition of 6N HCl
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried with Na2SO4
  6. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-865283bddc8648c4ac57f90acc6f2986
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08946278B2

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