Methanol → HCID 69889855, Verbindung

HRID 2119438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2119438
[CH3:1][C:2]1[CH:6]=[C:5](C(OCC)=O)[N:4]([C:12]2[C:21]([F:22])=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[N:3]=1.O[Li].[OH2:25].[OH2:26].[CH3:27]O>>[CH3:27][C:2]1([C:1]([OH:26])=[O:25])[CH:6]=[CH:5][N:4]([C:12]2[C:21]([F:22])=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[NH:3]1

Komponenten

5

Edukt 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 22728901ethyl 3-methyl-1-(3-fluoro-2-naphthyl)-1H-pyrazole-5-carboxylate

Produkt 1

HCID 69889855HCID 69889855, VerbindungAusbeute 90 %

Versuchsvorschrift

The preparation of ethyl 3-methyl-1-(3-fluoro-2-naphthyl)-1H-pyrazole-5-carboxylate was the same as that in Step 3 for Example 3. This ester (13.2 g, 44 mmol) was dissolved in 80 mL methanol. To it were added LiOH.H2O (3.7 g, 49 mmol) and 40 mL water. The mixture was stirred for overnight at room temperature. It was evaporated in vacuuo to remove methanol. The residue was acidified with 1N HCl till pH 1. The mixture was extracted with EtOAc (×4). The organic extracts were combined, dried, evaporated and pumped to dryness to afford 3-methyl-1-(3-fluoro-2-naphthyl)-1H-pyrazolecarboxylic acid in over 90% yield. ES-MS: (M+H)+ 271.

Aufarbeitung

  1. customIt was evaporated in vacuuo
  2. customto remove methanol
  3. extractionThe mixture was extracted with EtOAc (×4)
  4. customdried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fa74d8e88dd6465db1938a8b3a76cce3
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06686368B1

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