Methylhydrazine → ethyl 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)propanoate

HRID 220462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220462
[C:1]([CH:4]([C:12](=O)[CH3:13])[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH3:2].[CH3:15][NH:16][NH2:17]>C(O)(=O)C>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][C:4]1[C:12]([CH3:13])=[N:17][N:16]([CH3:15])[C:1]=1[CH3:2])[CH3:11]

Komponenten

4

Edukt 2

HCID 6061MethylhydrazineHCID 2733934Hexanoic acid, 4-acetyl-5-oxo-, ethyl ester

Produkt 1

HCID 16394809ethyl 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)propanoateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Dissolve ethyl 4-acetyl-5-oxohexanoate (2.00 g, 9.99 mmol) in acetic acid (21 mL). Add methyl hydrazine (589 μL, 10.99 mmol) and stir at room temperature for 18 hr. Concentrate and dissolve residue in ethyl acetate. Wash ethyl acetate layer with saturated aqueous sodium bicarbonate solution. Extract aqueous layer twice with ethyl acetate, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 100% ethyl acetate:hexanes) to give 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-propionic acid ethyl ester (1.95 g, 93%). MS (ES): m/z=211 [M+H]+.

Aufarbeitung

  1. concentrationConcentrate
  2. dissolutiondissolve residue in ethyl acetate
  3. dry with materialExtract aqueous layer twice with ethyl acetate, dry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 0:100 to 100% ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-000c6f90b8f246098496a859eabe70f4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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