Sodium Hydroxide → 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylic acid

HRID 1191169

Reaktionsgleichung

Reaktionsgleichung von HRID 1191169
C([O:3][C:4]([C:6]1[N:7]([CH3:16])[N:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[Cl:11])=[O:5])C.[OH-].[Na+]>CO>[C:12]([C:9]1[C:10]([Cl:11])=[C:6]([C:4]([OH:5])=[O:3])[N:7]([CH3:16])[N:8]=1)([CH3:15])([CH3:13])[CH3:14]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67412028ethyl 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylate

Produkt 1

HCID 584254493-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (prepared as described in the previous step, 2.20 g, 9.00 mmol) and 3 N aqueous NaOH (7.50 mL, 22.5 mmol) in MeOH (40 mL) was stirred at room temperature for 4 h. The solvent was removed under reduced pressure, and the residue was treated with H2O (30 mL) and washed with Et2O. The aqueous layer was then acidified to pH 7 by 2 N aqueous HCl and extracted with DCM. The combined organic layers were washed with brine and dried with Na2SO4. The solvent was removed in vacuo to yield the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 10.41 (br s, 1H), 4.12 (s, 3H), 1.42 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated for C9H13ClN2O2: 217.1 (M+H), Measured: 217.1.

Aufarbeitung

  1. customprepared
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was treated with H2O (30 mL)
  4. washwashed with Et2O
  5. extractionextracted with DCM
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried with Na2SO4
  8. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cb2ea08002074bffab2c4d2ef85d21b9
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680098B2

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