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

Temperatur

-78 °C

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.

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)

ORD-Eintrag

ord-3c651f8445aa49279d7c6c5346361ebe

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08101637B2