Hydrochloric Acid → 4-Methylpyridine-2-carbaldehyde

HRID 742469ノート

反応式

HRID 742469 の反応式
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N+:4]=1[O-])#N.Cl.O.C(=O)(O)[O-:14].[Na+]>C(Cl)Cl>[CH3:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH:1]=[O:14])[CH:8]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 37251652-Cyano-4-methylpyridin-1-ium-1-olate

生成物 1

HCID 100118944-Methylpyridine-2-carbaldehyde収率 14.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2-cyano-4-methylpyridine-N-oxide (3.29 g, 0.0279 mol) in 164 mL of methylene chloride at -78° C. was added 27.6 mL of DIBAL(H) and the mixture was stirred at -78 ° C. for 2 h. To the above mixture was added 13 mL of HCl (conc.) and 52 mL of water, and the mixture was warmed to room temperature. To the aqueous layer was added sodium bicarbonate solution, the solution was extracted with ether, and the combined organic layer was concentrated in vacuo. The residue was purified by chromatography on silica (ether) to afford 0.5 g (14.8%) of 4-methylpyridine-2-carboxaldehyde, as an oil.

後処理

  1. temperaturethe mixture was warmed to room temperature
  2. extractionthe solution was extracted with ether
  3. concentrationthe combined organic layer was concentrated in vacuo
  4. customThe residue was purified by chromatography on silica (ether)

出典と根拠

ORDレコード
ord-fd273ddc774046a78311e8788a0eaf7b
出典データセット
uspto-grants-1996_09
特許番号
US05554620

反応ノート

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