反应详情

温度

5 °C

To a solution of NaH (60% in mineral oil, 259 mg, 6.47 mmol) in THF (10 mL) cooled to 5° C. under nitrogen a solution of 6-ethyl-1H-indole-3-carbaldehyde (1.12 g, 6.47 mmol) in THF (20 mL) was slowly added and the mixture was stirred at 5° C. for 30 min. While maintaining the internal temperature between 5° C. and 10° C., chlorosulfonyl isocyanate (1.12 mL, 12.9 mmol) was added dropwise and the solution was further stirred at RT overnight. Acetic acid (15 mL) was added (slightly exothermic) and the solution was stirred at RT for 1.5 h. Ice cubes and water (25 mL) were added, and the solution was further stirred at RT for 30 min. Water was added and the mixture was extracted with EtOAc. The aqueous layer was back-extracted twice with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to EtOAc) to give the desired compound. LC/MS: 290.0 [M+H]+, 312.0 [M+Na]+; tR (HPLC conditions a): 3.02 min.

1. additionwas slowly added
2. additionwas added dropwise
3. stirringthe solution was further stirred at RT overnight
4. stirringwas stirred at RT for 1.5 h
5. stirringthe solution was further stirred at RT for 30 min
6. extractionthe mixture was extracted with EtOAc
7. extractionThe aqueous layer was back-extracted twice with EtOAc
8. dry with materialThe combined organic layers were dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to EtOAc)