Dimethylformamide → (E)-Ethyl 3-(1-methyl-1H-pyrazol-4-yl)acrylate

HRID 30681

Reaktionsgleichung

Reaktionsgleichung von HRID 30681
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=O)[CH:4]=[N:3]1.[H-].[Na+].C(OP([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(OCC)=O)C.CN(C)C=O>O>[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:4]=[N:3]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 5731171-Methyl-1H-pyrazole-4-carbaldehyde

Produkt 1

HCID 68356132(E)-Ethyl 3-(1-methyl-1H-pyrazol-4-yl)acrylateAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1-methyl-1H-pyrazole-4-carbaldehyde (2.59 g), sodium hydride (60% in oil, 1.13 g), ethyl diethylphosphonoacetate (5.8 g) and N,N-dimethylformamide (50 ml) was stirred at room temperature for 2 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give ethyl (2E)-3-(1-methyl-1H-pyrazol-4-yl)acrylate (2.72 g, 64%) as crystals from a fraction eluted with hexane-ethyl acetate (1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 43-44° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1bd55c209f4d461382b28eb878c6df98
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423159B2

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