Methylhydrazine → ethyl 2-(1,3,5-trimethyl-1H-pyrazol-4-yl)acetate

HRID 220457

Reaktionsgleichung

Reaktionsgleichung von HRID 220457
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH:6]([C:10](=O)[CH3:11])[C:7](=O)[CH3:8])[CH3:2].[CH3:14][NH:15][NH2:16]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:10]([CH3:11])=[N:16][N:15]([CH3:14])[C:7]=1[CH3:8])[CH3:2]

Komponenten

4

Edukt 2

HCID 6061MethylhydrazineHCID 87820Ethyl 3-acetyl-4-oxopentanoate

Produkt 1

HCID 16394807ethyl 2-(1,3,5-trimethyl-1H-pyrazol-4-yl)acetateAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Dissolve 3-acetyl-4-oxopentanoic acid ethyl ester (3.35 g, 19.5 mmol) in glacial acetic acid (20 mL) and add methylhydrazine (1.13 mL, 21.4 mmol) dropwise. Stir the resulting mixture at room temperature for 16 hr. Concentrate and partition the residue between ethyl acetate (100 mL) and saturated aqueous sodium bicarbonate solution (50 mL). Separate organic layer, dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 7:3 hexanes:ethyl acetate) to give (1,3,5-trimethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (2.8 g, 73%) as an oil. 1H NMR (CDCl3) δ 4.08 (q, 2H), 3.67 (s, 3H), 3.29 (s, 2H), 2.18 (s, 6H), 1.21 (t, 3H).

Aufarbeitung

  1. concentrationConcentrate
  2. custompartition the residue between ethyl acetate (100 mL) and saturated aqueous sodium bicarbonate solution (50 mL)
  3. dry with materialSeparate organic layer, dry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 7:3 hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2d95a319eeab4885851635057c0e2465
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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