Water → 5-methyl-1H-pyrazole-3-carboxylic acid

HRID 1527953

Reaktionsgleichung

Reaktionsgleichung von HRID 1527953
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[N:7]=1)=[O:5])C.[Li+].[OH-].O>CCO>[CH3:11][C:9]1[NH:8][N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=1.[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[C:13]([CH:18]=1)[CH2:12][N:8]1[C:9]([CH3:11])=[CH:10][C:6]([C:4]([OH:5])=[O:3])=[N:7]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 866887261-[5-Chloro-2-(4-methoxy-benzyloxy)-benzyl]-5-methyl-1h-pyrazole-3-carboxylic acid ethyl ester

Produkt 2

HCID 98225-methyl-1H-pyrazole-3-carboxylic acidHCID 866887271-[5-Chloro-2-(4-methoxy-benzyloxy)-benzyl]-5-methyl-1h-pyrazole-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 1-[5-chloro-2-(4-methoxy-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester, 13, 0.28 g (0.6 mmol) in EtOH (2 mL) was added a solution of LiOH (0.15 g in 0.5 ml H2O). The resulting mixture was heated at 100° C. on microwave for 10 minutes. The mixture was poured into water (20 mL) and extracted with EtOAc (3×15 mL). The organic layers were combined, washed with brine (30 mL), dried (MgSO4) and the volatiles removed in vacuo to yield 5-chloro-2-(4-methoxy-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carboxylic acid, 14 as a white solid.

Aufarbeitung

  1. extractionextracted with EtOAc (3×15 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customthe volatiles removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e0f1287c1e904c04b28f09b440974206
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090566B2

Verknüpfte Notizen

Wird geladen…