反应详情

温度

15 °C

To a solution of 2,2-dimethyl-N-o-tolyl-propionamide (30.0 g, 159 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.5 M, in hexane, 190 mL) at 15° C. The mixture was stirred overnight at 15° C., cooled in an ice-water bath and treated with saturated NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography to give 2-tert-butyl-1H-indole (23.8 g, 88%).

1. temperaturecooled in an ice-water bath
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with ethyl acetate
4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuum
7. customThe residue was purified by column chromatography