Sodium Chloride → 4-Methylpyridine-3-carbaldehyde

HRID 1421683노트

반응식

HRID 1421683 반응식
[Li]CCCC.C[N:7]([CH3:12])[CH2:8][CH2:9]NC.N1C=[CH:17][CH:16]=[C:15]([CH:19]=[O:20])C=1.IC.[Na+].[Cl-]>C1COCC1>[CH3:17][C:16]1[CH:9]=[CH:8][N:7]=[CH:12][C:15]=1[CH:19]=[O:20]

참가 물질

7

반응물 5

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 103713-PyridinecarboxaldehydeHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 178418339Butyllithium2회

생성물 1

HCID 124604704-Methylpyridine-3-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

n-BuLi (1.6M in hexanes) (2.2 mmol, 1.37 ml) was added dropwise to a stirred solution of N,N,N'-trimethylethylenediamine (2.4 mmol, 0.245 g) in THF at -78° C. A solution of 3-pyridinecarboxaldehyde (2 mmol, 0.214 g) in THF was added and the mixture stirred for 15 min before adding a further portion of n-BuLi (1.6M in hexanes) (4 mmol, 2.5 ml). After stirring for 2 h at -70° C., iodomethane was added, the mixture stirred at RT for 30 min, then poured into aqueous NaCl solution, extracted twice with Et2O, dried (MgSO4), filtered and concentrated in vacuo. The residue was subjected to chromatography (SiO2 ; Et2O) to afford the title compound as an oil.

후처리

  1. stirringAfter stirring for 2 h at -70° C.
  2. stirringthe mixture stirred at RT for 30 min
  3. extractionextracted twice with Et2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8489366b140149dd8003d304e2903011
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077854

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