Benzaldehyde → 3-(2-Phenylethenyl)pyridazine

HRID 990248

反応式

HRID 990248 の反応式
[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

参加物

4

反応物 2

HCID 240BenzaldehydeHCID 742083-Methylpyridazine

生成物 1

HCID 2500313-(2-Phenylethenyl)pyridazine収率 59%

試薬・触媒・溶媒 1

HCID 3007855Zincchloride触媒

反応条件

温度
150 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-68a68af14f8940a398e548916c46430f
出典データセット
uspto-grants-2002_10
特許番号
US06458951B2

関連ノート

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