反应详情

2-Ethyl-1,5,6,7-tetrahydro-1-(2-phenyl-phenylmethyl)-4H-indol-4-one (2.17 g, 0.0066 mol) dissolved in 10 mL of tetrahydrofuran was added to a slurry of sodium hydride (0.58 g) in 3 mL of tetrahydrofuran and the mixture was stirred for 15 min at room temperature. Methyl benzene sulfinate (1.13 g) was added and the solution stirred overnight. The reaction mixture was poured into water, the pH adjusted to 6 with acetic acid and extracted with toluene. The organic layer was separated, washed with water and brine, dried with sodium sulfate, concentrated, taken up in toluene (80 mL) and heated at reflux for 1.5 h. After cooling, the mixture was concentrated, dissolved in ether (100 mL), washed with saturated sodium bicarbonate solution, dried over sodium sulfate, concentrated and purified by flash chromatography on silica eluting with 10:1 hexane/ethyl acetate to afford 0.85 g of subtitled material.

1. stirringthe solution stirred overnight
2. extractionextracted with toluene
3. customThe organic layer was separated
4. washwashed with water and brine
5. dry with materialdried with sodium sulfate
6. concentrationconcentrated
7. temperatureheated
8. temperatureat reflux for 1.5 h
9. temperatureAfter cooling
10. concentrationthe mixture was concentrated
11. dissolutiondissolved in ether (100 mL)
12. washwashed with saturated sodium bicarbonate solution
13. dry with materialdried over sodium sulfate
14. concentrationconcentrated
15. custompurified by flash chromatography on silica eluting with 10:1 hexane/ethyl acetate