Hydrochloric Acid → HCID 18470723, compound

Temperature

85 °C

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.

1. temperatureAfter cooling
2. extractionThe whole was extracted with ethyl acetate (150 mL×2)
3. washthe combined organic layers were washed with brine (50 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vactio
6. additiona 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
7. temperatureheated
8. temperatureat reflux temperature for 15 minutes
9. temperatureAfter cooling
10. extractionthis mixture was extracted with ethyl acetate (100 mL×2)
11. washThe combined organic layers were washed with brine (50 mL)
12. dry with materialdried over MgSO4
13. concentrationconcentrated in vacuo
14. customThe residue was recrystallized from ethyl acetate-hexane

ORD record

ord-60d89d2733974fc2897f8127567cb588

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06417202B1