Hydrochloric Acid → 4-Methylpyridine-2-carbaldehyde

HRID 742469

반응식

HRID 742469 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 100118944-Methylpyridine-2-carbaldehyde수율 14.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fd273ddc774046a78311e8788a0eaf7b
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554620

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