Dichloromethane → HCID 69275389, compound

Participants

Reaction Steps

To a solution of 3-acetyl-1-(2,4-dimethoxyphenyl)-2,5-dimethylpyrrole (2.73 g, 10 mmol) (EXAMPLE 33) in CH2Cl2at rt (75 mL) was added a 1.0M solution of boron tribromide in CH2Cl2 (15 mL, 15 mmol) and the reaction monitored by LC. After complete consumption of the starting material, the reaction was carefully quenched with saturated NaHCO3 and partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by flash chromatography to give 3-acetyl-2,5-dimethyl-1-(4-hydroxy-2-methoxyphenyl)pyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 6.92 (d, 1H), 6.61 (d, 1H), 6.54 (dd, 1H), 6.32 (s, 1H), 3.72 (s, 3H), 2.44 (s, 3H), 2.26 (s, 3H), 1.93 (s, 3H), 1.69 (br s, 1H); MS (ESI) 260 (M+H)+.

Provenance & Evidence