Hydrochloric Acid → HCID 18470723, compound

Participants

Reaction Conditions

Reaction Steps

3-Acetyl-2,4-dimethyl-5-(4-pyridyl)-1-{2-(trimethylsilyl)ethoxymethyl}-1H-pyrrole (1.12 g, 3.39 mmol) was dissolved with EtOH (10 mL) and 10% aqueous HCl solution (30 mL) and the mixture was heated at 85° C. for 4 hours. After cooling, the mixture was neutralized with saturated aqueous NaHCO3 solution. The whole was extracted with ethyl acetate (150 mL×2), and the combined organic layers were washed with brine (50 mL), dried over MgSO4, and concentrated in vactio. The resulting solid was a mixture of 3-acetyl-1-hyroxymethyl-2,4-dimethyl-5-(4-pyridyl)-1H-pyrrole and 3-acetyl-2,4-dimethyl-5-(4-pyridyl)-1H-pyrrole. This mixture was suspended with saturated aqueous sodium acetate solution and then heated at reflux temperature for 15 minutes. After cooling, this mixture was extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with brine (50 mL), dried over MgSO4, and concentrated in vacuo. The residue was recrystallized from ethyl acetate-hexane to give the title product (205 mg, 28% yield) as a pale yellow solid.

Provenance & Evidence