Methyl iodide → 2-Ethylquinoline

HRID 33775

反応式

HRID 33775 の反応式
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]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 70602-MethylquinolineHCID 7912DiisopropylamineHCID 178418339Butyllithium

生成物 1

HCID 1371132-Ethylquinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b46e68255d4c420991e21cad2ba93f5c
出典データセット
uspto-grants-2008_09
特許番号
US07429666B2

関連ノート

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