Hydrochloric Acid → 5-Acetyl-2-methoxypyridine

Temperature

110 °C

2-Methoxybromopyridine (25 g) and n-butyl vinyl ether (66.6 g) were dissolved in DMF (250 ml). To the solution were added 1,3-bis(diphenylphosphino)propane (3.62 g) and Pd(OAc)2 (896 mg) and aq. K2CO3 under nitrogen atmosphere. The reaction mixture was stirred for 2 hours at 100-120° C. The mixture was cooled to 25° C. To the solution was added 1N aq. HCl (625 ml). The solution was stirred for 1 hour at 25-30° C. The solution was portioned to EtOAc and water. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic solution was washed with water and brine, and dried over MgSO4. Evaporation of solvent in vacuo gave oily residue. The residue was purified by chromatography on silica gel (EtOAc:n-Hexane=1:5, v/v) to give 2-methoxy-5-acetylpyridine as a solid (12.14 g).

1. temperatureThe mixture was cooled to 25° C
2. stirringThe solution was stirred for 1 hour at 25-30° C
3. customThe organic layer was separated
4. extractionThe aqueous layer was extracted with EtOAc
5. washThe combined organic solution was washed with water and brine
6. dry with materialdried over MgSO4
7. customEvaporation of solvent in vacuo
8. customgave oily residue
9. customThe residue was purified by chromatography on silica gel (EtOAc

ORD record

ord-f700468174db4ab7be791ccca4e4ee83

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07407961B2