Methyl iodide → 2-Ethylquinoline

HRID 33775

반응식

HRID 33775 반응식
C(NC(C)C)(C)C.[Li][CH2:9][CH2:10][CH2:11][CH3:12].[N:13]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=CC=1C.CI>C1COCC1>[CH2:11]([C:10]1[CH:9]=[CH:17][C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:13]=1)[CH3:12]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 70602-MethylquinolineHCID 7912DiisopropylamineHCID 178418339Butyllithium

생성물 1

HCID 1371132-Ethylquinoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a 0.40 M solution of diisopropyl amine in THF at −10° C. was added slowly 1.0 equiv of a solution of n-BuLi (2.5 M/hexane). After 10 min, the mixture was cooled to −78° C. and 0.9 equiv of quinaldine was added dropwise. The red/orange solution was then stirred at 0° C. for 1 h. MeI was then added and the reaction was stirred at room temperature for 2 h. The reaction was quenched with aqueous NH4Cl solution, and then extracted with EtOAc. The organic phase was washed with H2O and brine. The solution was then dried (MgSO4), filtered, and evaporated. The crude material was purified by flash chromatography with 1:10 EtOAc:hexanes to give the title compound as a pale yellow oil.

후처리

  1. stirringthe reaction was stirred at room temperature for 2 h
  2. customThe reaction was quenched with aqueous NH4Cl solution
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialThe solution was then dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude material was purified by flash chromatography with 1:10 EtOAc

출처 및 근거

ORD 기록
ord-b46e68255d4c420991e21cad2ba93f5c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429666B2

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