反应详情

温度

0 °C

Via addition funnel slowly add over 0.5 hours the 2M EtOEt solution of cyclopropyl magnesium bromide (2.16 g, 6.23 ml, 12.46 mmol, 1.1 eq) to the −78° C. THF solution (30 ml) of 4-(3-Iodo-indole-1-sulfonyl)-benzoic acid methyl ester (5 g, 11.33 mmol, 1.00 eq). Stir for 2 hours and then warm to 0° C. Stir for 0.5 hours. Recool to −10° C. and then slowly add a THF solution (3 ml) of cyclohexanone (1.298 g, 13.03 mmol, 1.15 eq). Stir for 15 min and warm to room temperature. Stir for 1.5 days. Quench reaction with saturated aqueous ammonium chloride, remove organics on rotovap, and add EtOAc to crude mix. Extract product into organics, separate organics, dry over MgSO4, and concentrate on rotovap to give crude product as an oil. Purify by silica gel chromatography to give 4-[3-(1-Hydroxy-cyclohexyl)-indole-1-sulfonyl]-benzoic acid methyl ester (948 mg, 20% yield).

1. additionVia addition funnel
2. stirringStir for 0.5 hours
3. customRecool to −10° C.
4. stirringStir for 15 min
5. temperaturewarm to room temperature
6. stirringStir for 1.5 days
7. customQuench
8. customreaction with saturated aqueous ammonium chloride
9. customremove organics on rotovap
10. additionadd EtOAc to crude
11. additionmix
12. customExtract product into organics, separate organics
13. dry with materialdry over MgSO4
14. concentrationconcentrate on rotovap
15. customto give crude product as an oil
16. customPurify by silica gel chromatography