Ethyl Acetate → HCID 15458948, compound

Participants

Reaction Steps

At room temperature, to a stirred solution of tert-butyl pyrrole-2-carboxylate (obtained from Step A) (120 mg, 0.718 mmol) dissolved in benzene (2.5 mL) was added tetra-N-butylammonium hydrogen sulfate (49 mg, 0.144 mmol) followed by 50% aqueous sodium hydroxide solution (0.72 mL). After 10 min, a solution of 3,5-dichlorobenzenesulfonyl chloride (264 mg, 1.08 mmol) dissolved in benzene (1 mL) was added dropwise via a gas-tight syringe over a 25 min period. The reaction mixture was allowed to stir overnight at room temperature. Ethyl acetate and water were added and the phases were separated. The aqueous layer was re-extracted twice with ethyl acetate and the combined organic layers were washed with water (3×) and dried over anhydrous sodium sulfate. The crude product obtained after filtration and removal of solvents by rotoevaporation was purified by flash column chromatography on silica gel eluted with 0.5-2.5% ethyl acetate in hexane to afford the title compound (104 mg), homogeneous by TLC in 10/1 hexane/ethyl acetate; 77% yield, based on starting material consumed) and recovered starting material (58 mg, 50%).

Provenance & Evidence