Methyl iodide → 2-Ethylquinoline

sec-Butyllithium (1.3 M in cyclohexane, 19.3 mL, 25.1 mmol, 1.2 eq.) was added dropwise to a 0° C. solution of 2-methylquinoline (2.84 mL, 3.0 g, 21.0 mmol, 1.0 eq.) in dry diethyl ether (75 mL). After the addition was complete the cooling bath was removed and the mixture was stirred at r.t. for 1.5 h. The reaction mixture was cooled to 0° C. and methyl iodide (1.96 mL, 4.46 g, 31.4 mmol, 1.5 eq.) was added dropwise. After the addition was complete the cooling bath was removed and the reaction was stirred at r.t. for 3 h. Water (50 mL) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with brine (50 mL) and were dried over sodium sulfate and concentrated under reduced pressure which gave the crude product (4.82 g) as an orange oil. The crude product was purified by column chromatography (SiO2, 1:5 ethyl acetate-cyclohexane) which yielded the product (3.03 g, 92% yield) as a clear yellow oil; 1H NMR (500 MHz, CDCl3) δ 1.41 (t, J=7.5 Hz, 3H, CH3), 3.01 (q, J=7.5 Hz, 2H, CH2), 7.31 (d, J=8.5 Hz, 1H, Ar), 7.48 (t, J=7.5 Hz, 1H, Ar), 7.68 (t, J=7.5 Hz, 1H, Ar), 7.77 (d, J=8.0 Hz, 1H, Ar), 8.04 (d, J=8.5 Hz, 1H, Ar), 8.07 (d, J=8.5 Hz, 1H, Ar).

1. additionAfter the addition
2. customwas removed
3. temperatureThe reaction mixture was cooled to 0° C.
4. additionAfter the addition
5. customwas removed
6. stirringthe reaction was stirred at r.t. for 3 h
7. additionWater (50 mL) was added
8. customthe layers were separated
9. extractionThe aqueous layer was extracted with ethyl acetate (2×30 mL)
10. washThe combined organic extracts were washed with brine (50 mL)
11. dry with materialwere dried over sodium sulfate
12. concentrationconcentrated under reduced pressure which
13. customgave the crude product (4.82 g) as an orange oil
14. customThe crude product was purified by column chromatography (SiO2, 1:5 ethyl acetate-cyclohexane) which

ORD-Eintrag

ord-c0a3d221c51a44aababe0ebbdf9233e6

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09388138B2