Lithium Hydroxide → 1-(4-Methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylic acid

HRID 610130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 610130
[OH-].[Li+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]([O:18]C)=[O:17])=[CH:14][C:13]([S:20][CH3:21])=[N:12]2)=[CH:7][CH:6]=1>CO>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]([S:20][CH3:21])=[N:12]2)=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 18177273methyl 1-(4-methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylate

Produkt 1

HCID 181773011-(4-Methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylic acidAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of lithium hydroxide (4.5 mL, 1.0 M, 4.5 mmol) was added to a suspension of methyl 1-(4-methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylate (840 mg, 3.0 mmol) in MeOH (30 mL) and stirred at room temperatureerature for 21 hours. The resulting mixture was concentrated and partitioned between EtOAc and H2O. The organic layer was removed, and the aqueous layer was acidified with 1M HCl and extracted twice with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and evaporated to yield clean product (784 mg, 98%). 1H NMR (CDCl3): δ7.33 (d, 2H, J=8.4), 6.97 (s, 1H), 6.95 (d, 2H, J=8.4), 3.85 (s, 3H), 2.55 (s, 3H).

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated
  2. custompartitioned between EtOAc and H2O
  3. customThe organic layer was removed
  4. extractionextracted twice with EtOAc
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ae3a38d5586a43b5b849de888d304f20
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998424

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