Trifluoroacetic acid → Diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of diethyl (5-benzoylpyrrol-2-yl)-acetoxymethanedicarboxylate (142 mg, 0.367 mmol) and triethylsilane (102 mg, 0.440 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (84 mg, 0.734 mmol). The reaction mixture was stirred at 40° C. for 24 hours. Additional triethyl silane (51 mg, 0.220 mmol) and trifluoroacetic acid (84 mg, 0.734 mmol) was added. The reaction mixture was stirred at 40° C. for an additional 24 hours. The mixture was cooled to room temperature, washed with cold 10% aqueous sodium hydroxide and saturated aqueous sodium chloride, and concentrated under reduced pressure. The residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (87:13) to provide 60 mg (50%) of diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate.

Provenance & Evidence