反应详情

To a suspension of LiAlH4 (7.6 g, 0.2 mol) in dioxane (100 mL) is added dropwise a solution of methyl 6-methoxy-1H-indole-2-carboxylate (8.2 g, 0.04 mol) in dioxane (50 mL) at 0° C. After the addition, the mixture is stirred at room temperature for 1 h and then heated at reflux for 5 h. After cooling to 0° C., the reaction is quenched by water (dropwise) and then 15% aqueous NaOH. After stirring at room temperature for 1 h, the mixture is filtered through Celite. The solid is washed with a large amount of EtOAc. The solvent is washed with brine, dried over Na2SO4 and evaporated under vacuum. The residue is purified by flash column chromatography on silica gel using EtOAc/petroleum ether (1/5) as eluent to yield 61% of 6-methoxy-2-methyl-1H-indole.

1. additionAfter the addition
2. temperatureheated
3. temperatureat reflux for 5 h
4. temperatureAfter cooling to 0° C.
5. customthe reaction is quenched by water (dropwise) and then 15% aqueous NaOH
6. stirringAfter stirring at room temperature for 1 h
7. filtrationthe mixture is filtered through Celite
8. washThe solid is washed with a large amount of EtOAc
9. washThe solvent is washed with brine
10. dry with materialdried over Na2SO4
11. customevaporated under vacuum
12. customThe residue is purified by flash column chromatography on silica gel