反应详情

温度

10 °C

10.3 g (40 mmol) of 1-(phenylsulfonyl)indole (synthesized analogous to T. Sakamoto; Y. Kondo; N. Takazawa; H. Yamanaka; J.Chem.Soc.Perkin Trans.1; 16; 1996; 1927-1934) in 110 ml tetrahydrofuran were cooled to −20° C. To the stirred solution 30 ml of 1.6 M n-butyllithium were added at −20° C. within 20 min. The resulting suspension was warmed to 10° C. and stirred at 10° C. for 4 hours. The mixture was again cooled to −20° C. and a solution of 3.4 g acrolein (61 mmol) in 20 ml THF was added dropwise within 20 min at −20° C. The solution was stirred at 20° C. for 16 hours. 150 ml water was added dropwise, the mixture was vigorously stirred for 10 min. The phases were separated, and the water phase was extracted with 3×100 ml of methyl-t-butyl-ether. The combined organic phases were washed with 100 ml of brine, dried on sodium sulfate and rotary evaporated (35° C., 20 mbar). The residue was purified by liquid chromatography (eluent toluene/ethyl acetate 6:1), the pure fractions were collected and rotary evaporated (40° C./15 mbar).

1. temperatureThe mixture was again cooled to −20° C.
2. stirringThe solution was stirred at 20° C. for 16 hours
3. stirringthe mixture was vigorously stirred for 10 min
4. customThe phases were separated
5. extractionthe water phase was extracted with 3×100 ml of methyl-t-butyl-ether
6. washThe combined organic phases were washed with 100 ml of brine
7. customdried on sodium sulfate
8. customrotary evaporated (35° C., 20 mbar)
9. customThe residue was purified by liquid chromatography (eluent toluene/ethyl acetate 6:1)
10. customthe pure fractions were collected
11. customrotary evaporated (40° C./15 mbar)