Hydrochloric Acid → Ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate

Participants

Reaction Steps

To a suspension of aluminum chloride (26.3 g, 198 mmol) in t-butanethiol (60 ml) at 0° C. was added a solution of ethyl 3-(1-(4-chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl)-2,2-dimethylpropionate (32 g, 66 mmol), prepared as in step 2, in methylene chloride (90 ml) and the reaction mixture was stirred at 0° C. for 10 min and at ambient temperature for 3 hours. The reaction mixture was then poured into ice and acidified with 10% aqueous hydrochloric acid. The organic layer was washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide a white solid. The solid was washed with 20% solution of ethyl ether in hexane and dried in vacuo to afford 21.8 g of ethyl 3-(1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl)-2,2-dimethylpropionate.

Provenance & Evidence