反应详情

Diethyl 1-diazo-2-oxopropylphosphonate (9.6 g, 1.2 eq.) was added to a solution of 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal (11.15 g, 41.7 mmol, 1 eq.) and potassium carbonate (11.6 g, 2 eq.) in methanol. The reaction mixture was stirred until analysis by TLC indicated that all of the starting material had been consumed. The reaction mixture was filtered and the filter cake was rinsed until clear. The filtrate was concentrated under reduced pressure to provide crude product as an oil. The oil was partitioned between dichloromethane (200 mL) and water (100 mL). The organic layer was washed sequentially with water and brine (2×100 mL) and then concentrated under reduced pressure to provide 8.8 g of 2-ethyl-1-(4-pentynyl)-1H-imidazo[4,5-c]quinoline.

1. customhad been consumed
2. filtrationThe reaction mixture was filtered
3. washthe filter cake was rinsed until clear
4. concentrationThe filtrate was concentrated under reduced pressure
5. customto provide crude product as an oil
6. customThe oil was partitioned between dichloromethane (200 mL) and water (100 mL)
7. washThe organic layer was washed sequentially with water and brine (2×100 mL)
8. concentrationconcentrated under reduced pressure