3-Pyridinecarboxaldehyde → 3-(Oxiran-2-yl)pyridine

HRID 23712

반응식

HRID 23712 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[CH3:9]OS([O-])(=O)=O.C[S+](C)C.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[O:8]1[CH2:9][CH:7]1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 3

HCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 2760871Trimethylsulfonium methyl sulfate

생성물 1

HCID 133195613-(Oxiran-2-yl)pyridine수율 28.6%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2.59 g of 3-pyridinecarboxaldehyde and 62 mg of tetra-n-butylammonium bromide in 60 mL CH2Cl2 at room temperature is added a solution of 10.0 g of trimethylsulfonium methylsulfate in 15 mL H2O. The resulting solution is set stirring and cooled to 0° C. Aqueous NaOH (50% w/w; 40 mL) is added in portions while stirring and the mixture subsequently refluxed for 1 h. After cooling to room temperature, the mixture is filtered and the filtrate extracted with CH2Cl2. The combined extracts are dried over MgSO4, filtered, and concentrated to yield a red oil, which is subjected to Kugelrohr distillation under high vacuum at 150° C. to yield 838 mg of the title compound as a clear, light yellow oil.

후처리

  1. stirringwhile stirring
  2. temperaturethe mixture subsequently refluxed for 1 h
  3. temperatureAfter cooling to room temperature
  4. filtrationthe mixture is filtered
  5. extractionthe filtrate extracted with CH2Cl2
  6. dry with materialThe combined extracts are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a red oil, which
  10. distillationis subjected to Kugelrohr distillation under high vacuum at 150° C.

출처 및 근거

ORD 기록
ord-80408188b07545bfbcf381ecf1bc3f7b
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852731B2

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