Tetrabutylammonium Fluoride → HCID 18373336, compound

Participants

Reaction Steps

Methyl 4-({2-[1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl]ethyl}sulfonyl)benzoate (1 eq) was dissolved in THF (0.3M), followed by nBu4NF (1M in THF) (1.2 eq). The resulting mixture was stirred at rt for 3 hrs, then quenched with NH4Cl(aq). Extracted with EtOAc and washed with brine. Purified with prep plate and 1:3 EtOAc/Hexane as eluent to give methyl 4-({2-[1-benzhydryl-5-chloro-2-(hydroxymethyl)-1H-indol-3-yl]ethyl}sulfonyl)benzoate (light brown gum) in 95% yield.

Provenance & Evidence