Benzaldehyde → 3-(2-Phenylethenyl)pyridazine

HRID 990248

반응식

HRID 990248 반응식
[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

참가 물질

4

반응물 2

HCID 240BenzaldehydeHCID 742083-Methylpyridazine

생성물 1

HCID 2500313-(2-Phenylethenyl)pyridazine수율 59%

시약·촉매·용매 1

HCID 3007855Zincchloride촉매

반응 조건

온도
150 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-68a68af14f8940a398e548916c46430f
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458951B2

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