4-Methylpyridine → 1-(3-Methoxyphenyl)-2-(4-pyridyl)ethanone

To a solution of 4-methyl-pyridine (1.04 mL, 10.74 mmol) in anhydrous tetrahydrofuran (40 mL) at 0° C. a 1 M solution of sodium hexamethyldisilazide in tetrahydrofuran (21.5 mL, 21.5 mmol, 2 eq) was added dropwise and the reaction was stirred for 20 minutes. Neat methyl 3-methoxybenzoate (1.8 g, 10.74 mmol, 1 eq) was then added and the reaction was stirred at 0° C. for one hour. The reaction was poured into saturated ammonium chloride solution and, after basification with saturated aqueous NaHCO3, extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was taken up with n-hexane and filtered to give 1.75 g (72%) of the desired product as beige solid (1.775 g, 50%).

1. stirringthe reaction was stirred at 0° C. for one hour
2. extractionafter basification with saturated aqueous NaHCO3, extracted with ethyl acetate
3. washThe organic layer was washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. filtrationfiltered

ORD record

ord-6d51969d966040b2b5589d90636798f0

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524707B2