Hydrochloric Acid → HCID 86620736, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-[(4-fluorophenyl)sulfonyl]-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate (380 mg) was dissolved in tetrahydrofuran (15 mL), and the mixture was cooled to −78° C. A 1.5 mol/l solution (1.96 mL) of diisobutylaluminum hydride in toluene was added dropwise, and the mixture was further stirred at −78° C. for 1 hr. 1 mol/l Hydrochloric acid (20 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 15 min and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1). The obtained brown oil was dissolved in acetonitrile (5 mL), and the mixture was cooled to 0° C. Tetra-n-propylammonium perruthenate (34 mg), N-methylmorpholine N-oxide (172 mg) and molecular sieves 4A powder (500 mg) were added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate, and filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1) to give the title compound as a colorless oil (yield 210 mg, 62%).

Provenance & Evidence