4-Toluenesulfonyl chloride → HCID 86654672, compound

Participants

Reaction Steps

Triethylamine (2.1 mL, 15.22 mmol) was added to a solution of 2-(2-methyl-4-phenylpyrrol-1-yl)ethanol (1.53 g, 7.61 mmol) in dry dichloromethane (20 mL) at room temperature followed by the addition of p-toluene sulfonyl chloride (1.88 g, 9.89 mmol). The resulting reaction mixture was stirred for 16 h and then diluted with water (30 mL) and extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with water (2×25 mL), brine (2×25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo to yield the crude compound. Purification by column chromatography over silica gel (100-200 mesh) with gradient elution with 10-12% ethyl acetate in petroleum ether as eluent afforded 2-(2-methyl-4-phenyl-pyrrol-1-yl)ethyl 4-methylbenzenesulfonate (1.2 g, 44%) as a brownish white crystalline solid.

Provenance & Evidence