2-Methylquinoline → 2-(4-Trimethylsilanyl-but-3-ynyl)-quinoline

HRID 422355ノート

反応式

HRID 422355 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Li+].CC([N-]C(C)C)C.Br[CH2:21][C:22]#[C:23][Si:24]([CH3:27])([CH3:26])[CH3:25]>C1COCC1>[CH3:25][Si:24]([CH3:27])([CH3:26])[C:23]#[C:22][CH2:21][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

参加物

5

反応物 3

HCID 70602-MethylquinolineHCID 6425893-Bromo-1-(trimethylsilyl)-1-propyneHCID 2724682Lithium diisopropylamide

生成物 1

HCID 665984382-(4-Trimethylsilanyl-but-3-ynyl)-quinoline収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2-Methyl-quinoline (0.28 mL, 2.09 mmol) was added dropwise to a solution of LDA (3.0 mL, 0.8 M in THF) in THF (3 mL) at −78° C. and the reaction mixture was stirred for 1 hour at −78° C. Then (3-bromo-prop-1-ynyl)-trimethyl-silane (0.39 mL, 2.51 mmol) was added to the reaction mixture, the solution was stirred for 18 hours at room temperature and was quenched with water. The aqueous phase was extracted with DCM. The organic phase was washed with water, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1) to yield 338 mg (1.33 mmol, 64%) of 2-(4-trimethylsilanyl-but-3-ynyl)-quinoline as a yellow solid.

後処理

  1. stirringthe solution was stirred for 18 hours at room temperature
  2. customwas quenched with water
  3. extractionThe aqueous phase was extracted with DCM
  4. washThe organic phase was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1)

出典と根拠

ORDレコード
ord-3c651f8445aa49279d7c6c5346361ebe
出典データセット
uspto-grants-2012_01
特許番号
US08101637B2

反応ノート

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