Methyl iodide → 3,5-Dichloro-4-methylpyridine

HRID 54594

반응식

HRID 54594 반응식
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[Li+].[CH3:10]C([N-]C(C)C)C.[Li]CCCC.IC.C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:8])[C:7]=1[CH3:10]

참가 물질

8

반응물 5

HCID 6328Methyl iodideHCID 171533,5-DichloropyridineHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

생성물 1

HCID 109538273,5-Dichloro-4-methylpyridine수율 53%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

3,5-Dichloropyridine (2.04 g, 13.5 mmol) in THF (5 ml) was added dropwise to a solution of LDA [prepared from diisopropylamine (1.9 ml, 13.5 mmol) and n -BuLi (1.6M; 8.4 ml, 13.5 mmol)] in THF (25 ml) at -70° C. After stirring at this temperature for 5 min, iodomethane (0.85 ml, 13.5 mmol) was added and the reaction mixture stirred for a further 1.5h at -70° C. Saturated NaHCO3 (20 ml) and CH2Cl2 (20 ml) were added, the organic phase separated, dried (MgSO4), and concentrated in vacuo. The residue was subjected to chromatography (SiO2 ; Et2O/hexane, 1.:3) to afford the title compound (1.16 g) as a pale yellow solid. δH (CDCl3) 2.46 (3H, s, Me), and 8.36 (2H, s, pyridine H2, H6).

후처리

  1. customthe organic phase separated
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-18697e7a407540138991a8d1291cee5d
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622977

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