Methylhydrazine → ethyl 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylate

HRID 570181

Reaktionsgleichung

Reaktionsgleichung von HRID 570181
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3](=O)[CH2:4][C:5](=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:15][NH:16][NH2:17]>CCO>[CH2:9]([O:8][C:6]([C:5]1[N:16]([CH3:15])[N:17]=[C:3]([C:2]([CH3:14])([CH3:13])[CH3:1])[CH:4]=1)=[O:7])[CH3:10]

Komponenten

4

Edukt 2

HCID 6061MethylhydrazineHCID 83403Ethyl 5,5-dimethyl-2,4-dioxohexanoate

Produkt 1

HCID 2799344ethyl 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 5,5-dimethyl-2,4-dioxo-hexanoate (1.02 g, 5.09 mmol) was dissolved in absolute EtOH (20 mL). CH3NHNH2 (0.270 mL, 5.09 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 2 h. The resulting mixture was warmed to 80° C. for 4 h, and then cooled to room temperature. The solvent was removed under reduced pressure, and the resulting residue was chromatographed using a 70-g pre-packed SiO2 column eluting with 1:19 EtOAc-hexanes to yield the title compound as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ: 6.68 (s, 1H), 4.33 (q, J=7.2 Hz, 2H), 4.12 (s, 3H), 1.38 (t, J=7.1 Hz, 3H), 1.30 (s, 9H).

Aufarbeitung

  1. temperatureThe resulting mixture was warmed to 80° C. for 4 h
  2. temperaturecooled to room temperature
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting residue was chromatographed
  5. washeluting with 1:19 EtOAc-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7a24ec8aeddf43f5857cdaa9238abca3
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023846B2

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