반응 #10729

반응 방정식

iodomethane

1-(1H-indol-5-yl)-ethanone

iodomethane

cesium carbonate

→

1-(1-methyl-1H-indol-5-yl)-ethanone

수율 51.5%

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타The reaction was quenched with water
3. 3
   추출The aqueous solution was extracted with ether
4. 4
   세척The solution of ether was washed with saturated solution sodium bicarbonate, brine
5. 5
   건조dried over sodium sulfate
6. 6
   농축concentrated
7. 7
   기타The crude product was purified by flash chromatography
8. 8
   세척Elution with ethyl acetate (33%, v/v, in hexane)

실험 절차

Ex-28A: To a solution of 1-(1H-indol-5-yl)-ethanone (Yang, Y. et al, Heterocycles, 1992, 34(6), 1169–1175; 0.45 g, 2.8 mmol) were added iodomethane (3 mL) and cesium carbonate (2.3 g, 7.1 mmol). The reaction mixture was allowed to stir at 55° C. for 1.5 day during which additional iodomethane (11 mL) was added. The reaction was quenched with water. The aqueous solution was extracted with ether. The solution of ether was washed with saturated solution sodium bicarbonate, brine, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography. Elution with ethyl acetate (33%, v/v, in hexane) gave 1-(1-methyl-1H-indol-5-yl)-ethanone (0.25 g, 51%). 1H NMR (CDCl3) δ 8.30 (s, 1H), 7.91 (dd, J=1.2, 8.1 Hz, 1H), 7.34 (d, J=8.6 Hz, 1H), 7.12 (d, J=3.2 Hz, 1H), 6.61 (d, J=3.0, 1H), 3.82 (s, 3H), 2.66 (s, 3H).

출처