Toluene → [1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl](phenyl)methanone

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Reaction Steps

To a solution of 2,5-dimethyl-1-(4-ethoxyphenyl)pyrrole (EXAMPLE 1) (1.0 g, 4.7 mmol) and toluene (15 mL) at 0° C. was added dropwise SnCl4 (4.7 mL, 4.7 mmol, 1.0M solution in CH2Cl2) and benzoyl chloride (0.54 mL, 4.7 mmol). The mixture was warmed to rt and heated at 50° C. overnight. After cooling to rt, the mixture was diluted with 1N NaOH (50 mL), extracted with EtOAc (2×50 mL), the combined extracts washed with brine (50 mL), dried MgSO4), filtered, concentrated in vacuo, and purified by flash chromatography on silica gel (0-25% EtOAc/hexanes) to give 3-benzoyl-2,5-dimethyl-1-(4ethoxyphenyl)pyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 7.84-7.82 (m, 2H), 7.52-7.43 (m, 3H), 7.14-7.12 (m, 2H), 7.01-6.98 (m, 2H), 6.18 (s, 1H), 4.10 (q, 2H), 2.33 (s, 3H), 1.98 (s, 3H), 1.47 (t, 3H). MS (ESI) 320 (M+H)+.

Provenance & Evidence