Sulfuric Acid → 4-(3-Picolinoyltetrahydrofuran-3-yl)benzonitrile

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Reaction Steps

To a solution of 2-bromopyridine (0.412 g, 2.6 mmol) in dry THF was added n-BuLi (1.05 mL, 2.5 M solution in n-hexane) at −78° C. After stirring for 15 minutes, the solution of Example 79A (0.345 g, 1.74 mmol) in THF (2 mL) was added. The mixture was stirred at −78° C. for 15 minutes, then 5 mL of 1 M H2SO4 solution was added slowly. The mixture was heated at about 50° C.-60° C. for 30 minutes. The aqueous phase was separated and extracted with EtOAc (3×50 mL). The combined organic phases was washed with water (2×50 mL) and brine (50 mL) respectively, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (petroleum ether:EtOAc=3:1) to provide the title compound (65 mg, 13.4%). LC-MS: m/z 279 (M+H).

Provenance & Evidence