Trifluoroacetic acid → 5-[(Methylsulfonyl)methyl]-1H-indole

Participants

Reaction Steps

5-[(Methylsulfonyl)methyl]-2-(trimethylsilyl)-1H-indole (2) (1.5 g, 0.00534 mol) was dissolved in CH2Cl2 (70 mL). Trifluoroacetic acid (2 mL) was added and the mixture was stirred at RT for 2 h. The solvent was concentrated in vacuo and the residue was dissolved in EtOAc and extracted with sat. NaHCO3 and then with brine. The organic phase was dried over MgSO4, filtered and evaporate in vacuo. Silica gel chromatography (50-100% EtOAc gradient in hexane) of the concentrate gave the product 0.57 g, 51%) as a brown oil.

Provenance & Evidence