Dimethylformamide → ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate

HRID 349939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349939
[H-].[Na+].[CH2:3]([N:10]1[CH:14]=[C:13]([CH:15]=O)[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OP([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])(OCC)=O)C.CN(C)C=O>O>[CH2:3]([N:10]1[CH:14]=[C:13](/[CH:15]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 229307681-benzyl-3-(benzyloxy)-1H-pyrazole-4-carbaldehyde

Produkt 1

HCID 69421683ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydride (60%, oily, 1.94 g) was added to a mixture of 1-benzyl-3-benzyloxy-1H-pyrazole-4-carbaldehyde (12.90 g), ethyl diethylphosphonoacetate (9.60 ml), and N,N-dimethylformamide (200 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with diluted hydrochloric acid and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The crystals obtained were collected by filtration to yield ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate (14.50 g, yield: 91%). This was recrystallized from ethyl acetate-hexane. Melting point: 88–89° C.

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with diluted hydrochloric acid
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crystals obtained
  6. filtrationwere collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-08fa90de964c4beea62bd405a42ee8bd
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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