Benzaldehyde → 3-(2-Phenylethenyl)pyridazine

HRID 990248

Reaktionsgleichung

Reaktionsgleichung von HRID 990248
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]1[N:11]=[N:12][CH:13]=[CH:14][CH:15]=1>[Cl-].[Zn+2].[Cl-]>[C:2]1([CH:1]=[CH:9][C:10]2[N:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 240BenzaldehydeHCID 742083-Methylpyridazine

Produkt 1

HCID 2500313-(2-Phenylethenyl)pyridazineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007855ZincchlorideKatalysator

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Zinc chloride (820 mg, 6 mmol) was added to a stirred mixture of benzaldehyde (6.11 ml, 60 mmol) and 3-methylpyridazine (2.839, 30 mmol) and the resulting mixture heated for 20 hours at 150° C. The cool reaction mixture was partitioned between dichloromethane (40 ml) and 2M aqueous sodium hydroxide solution (20 ml), then the organic phase separated, combined with a dichloromethane extract (80 ml) of the aqueous phase, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using dichloromethane: methanol (99:1) as eluant, to give the title compound (59%) as a solid. δ (CDCL3): 7.12 (1H, d), 7.34 (3H, m), 7.56 (2H, d), 7.72 (1H, d), 8.37 (1H, s), 8.50 (1H, s), 8.60 (1H, s), LRMS: m/z 183 (M+1)+.

Aufarbeitung

  1. customThe cool reaction mixture
  2. customwas partitioned between dichloromethane (40 ml) and 2M aqueous sodium hydroxide solution (20 ml)
  3. customthe organic phase separated
  4. extractionextract (80 ml) of the aqueous phase
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-68a68af14f8940a398e548916c46430f
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458951B2

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