4-Methylpyridine → 1-Phenyl-2-(4-pyridinyl)ethanone

Temperature

0 °C

Lithium diisopropyl amide (16.9 mL, 1.5 M in cyclohexane, 25.4 mmol) was added to THF (40 mL) at −78° C. A solution of 4-picoline (2.50 mL, 25.4 mmol) in THF (30.0 mL) was added dropwise to the LDA solution. The dry ice bath was removed. The reaction mixture was stirred at 0° C. for 30 minutes, and cooled down to −78° C. A solution of N-methoxy-N-methylbenzamide (1) (5.00 g, 29.6 mmol) in THF (20.0 mL) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. The mixture was quenched with water, and extracted with ethyl acetate (3×). The pooled organic layer was dried over magnesium sulfate. The mixture was filtered, and the solvent was removed under vacuum to give the crude product. The crude material was triturated with hot hexane, and filtered to give 1-phenyl-2-(pyridin-4-yl)ethanone (2) as a yellow solid (3.53 g, 17.9 mmol, 70% yield).

1. customThe dry ice bath was removed
2. temperaturecooled down to −78° C
3. temperatureThe reaction mixture was warmed to room temperature
4. stirringstirred overnight
5. customThe mixture was quenched with water
6. extractionextracted with ethyl acetate (3×)
7. dry with materialThe pooled organic layer was dried over magnesium sulfate
8. filtrationThe mixture was filtered
9. customthe solvent was removed under vacuum
10. customto give the crude product
11. customThe crude material was triturated with hot hexane
12. filtrationfiltered

ORD record

ord-e8ccc6470c7d49c090013bb2ea5495a8

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809379B2