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

HRID 334631노트

반응식

HRID 334631 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0ef9c818c1fc4a4286f49bf45893e9ef
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883826B2

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