Tridecane → 2-Phenylpyridine

In a reaction flask was placed NiCl2(PCy3)2 (58.5 mg, 0.0847 mmol), tridecane (345 mg, 1.875 mmol, as an internal standard), and 2-methoxypyridine (343 mg, 3.146 mmol). The Grignard reagent (1 M in THF, 6.2 mmol) was added to the above catalyst mixture under a nitrogen atmosphere at 0° C. The resulting solution was stirred for several minutes and warmed to room temperature for 15 hours. The reaction mixture was quenched with an aqueous sodium citrate solution (1 M). The resulting aqueous solution was extracted with MTBE (4×25 mL). The combined organic layer was washed with an aqueous HCl solution (2.5 M, 4×15 mL). The aqueous layer was then extracted with MTBE (1×25 mL). This solution was cooled to 0° C. and a dilute aqueous KOH solution was added until pH 8. The aqueous layer was extracted with MTBE (4×25 mL) and dried over MgSO4. The resulting solution was filtered and concentrated under vacuum. The resulting residue was purified by silica gel chromatography (eluted with MTBE) to afford 2-phenylpyridine (368 mg, 75% yield).

1. customIn a reaction flask was placed
2. customThe reaction mixture was quenched with an aqueous sodium citrate solution (1 M)
3. extractionThe resulting aqueous solution was extracted with MTBE (4×25 mL)
4. washThe combined organic layer was washed with an aqueous HCl solution (2.5 M, 4×15 mL)
5. extractionThe aqueous layer was then extracted with MTBE (1×25 mL)
6. temperatureThis solution was cooled to 0° C.
7. additiona dilute aqueous KOH solution was added until pH 8
8. extractionThe aqueous layer was extracted with MTBE (4×25 mL)
9. dry with materialdried over MgSO4
10. filtrationThe resulting solution was filtered
11. concentrationconcentrated under vacuum
12. customThe resulting residue was purified by silica gel chromatography (eluted with MTBE)

ORD record

ord-f54d3f6f1bc04d8d91a068beba6922c9

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105467B2