Pyrrole → HCID 59430825, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of pyrrole (1.68 g) in toluene (40 mL) was added dropwise methyl magnesium bromide in THF (0.93N solution, 27.8 mL) at −20 to −30° C. After the addition, the reaction solution was further stirred for 30 minutes. A solution of methyl 4-[(2-pyridylsulfanyl)-carbonyl]benzoate (8.33 mmol) in toluene (80 mL) was cooled to −78° C., and thereto was added dropwise the above toluene solution via a cannula in such a manner that the temperature of the reaction mixture was not raised over −65° C. After the addition, the reaction solution was stirred at −78° C. for 2 hours, and thereto was added a saturated aqueous ammonium chloride solution (50 mL), and the mixture was warmed to room temperature. To the reaction solution was added ethyl acetate (100 mL), and the organic layer was separated. Further, the aqueous layer was extracted with ethyl acetate (50 mL×2). The organic layers were combined, and washed successively with 9% hydrochloric acid (100 mL), 10% aqueous sodium hydrogen carbonate solution (100 mL), water (100 mL) and a saturated brine (100 mL), dried over magnesium sulfate, filterd and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1→4/1) to give the title compound (1.40 g) as colorless solid.

Provenance & Evidence