反应详情

温度

0 °C

To a solution of lithium diisopropylamide prepared from diisopropylamine (1.11 g) and n-butyllithium (1.61 M in hexane; 7.0 ml), in dry tetrahydrofuran under nitrogen atmosphere at -70° C. was added dropwise over 20 minutes a solution of 3-methyl-1-phenylsulfonylindole (2.71 g) in tetrahydrofuran (20 ml). The mixture was stirred for 1 hour below -70° C. and then allowed to warm slowly to 0° C. over 1 hour. The resulting solution was cooled to -70° C. and then treated with ethylene oxide (484 mg) in dry tetrahydrofuran (5 ml). The mixture was stirred for 1 hour below -70° C. and then allowed to warm slowly to room temperature over 3 hours. After stirring overnight, the reaction mixture was treated with cold water and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed over silica gel (eluted with 5% ethyl acetate in toluene) to give 2-[3-methyl-1-(phenylsulfonyl)indol-2-yl]ethanol (1.19 g).

1. temperatureThe resulting solution was cooled to -70° C.
2. stirringThe mixture was stirred for 1 hour below -70° C.
3. temperatureto warm slowly to room temperature over 3 hours
4. stirringAfter stirring overnight
5. extractionextracted twice with ethyl acetate
6. washThe combined extracts were washed with brine
7. dry with materialdried over magnesium sulfate
8. customevaporated in vacuo
9. customThe residue was chromatographed over silica gel (eluted with 5% ethyl acetate in toluene)