(3-(Trifluoromethyl)phenyl)hydrazine → 3-Methoxymethyl-5-methyl-1-(3-trifluoromethyl-phenyl)-1h-pyrazole-4-carboxylic acid ethyl ester

HRID 1011951

Reaktionsgleichung

Reaktionsgleichung von HRID 1011951
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[CH2:13]([O:15][C:16](=[O:26])[CH:17]([C:23](=O)[CH3:24])[C:18](=O)[CH2:19][O:20][CH3:21])[CH3:14]>>[CH2:13]([O:15][C:16]([C:17]1[C:18]([CH2:19][O:20][CH3:21])=[N:10][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=2)[C:23]=1[CH3:24])=[O:26])[CH3:14]

Komponenten

3

Edukt 2

HCID 98650(3-(Trifluoromethyl)phenyl)hydrazineHCID 87352689Rac-2-acetyl-4-methoxy-3-oxo-butyric acid ethyl ester

Produkt 1

HCID 673137783-Methoxymethyl-5-methyl-1-(3-trifluoromethyl-phenyl)-1h-pyrazole-4-carboxylic acid ethyl esterAusbeute 25 %

Versuchsvorschrift

In analogy to the procedure described in Example 38A], 3-(trifluoromethyl)phenylhydrazine and rac-2-acetyl-4-methoxy-3-oxo-butyric acid ethyl ester gave after purification by flash column chromatography (CH2Cl2 to 5% Et2O/CH2Cl2) 5-methoxymethyl-3-methyl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester and in 25% yield as light brown solid. MS: 343.0 (MH+) and 3-methoxymethyl-5-methyl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester and in 36% yield as orange oil. MS: 343.0 (MH+).

Aufarbeitung

  1. customgave
  2. customafter purification by flash column chromatography (CH2Cl2 to 5% Et2O/CH2Cl2) 5-methoxymethyl-3-methyl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Quellen und Nachweise

ORD-Eintrag
ord-855a37bc5e70499c8a34f103fe4a586c
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977358B2

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