Phenol → HCID 62472276, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tributylphosphine (4.57 g, 22.63 mmol) in anhydrous tetrahydrofuran (20 mL) was added diisopropyl azodicarboxylate (4.57 g, 22.63 mmol) at 0° C. The reaction mixture was stirred for 10 minutes at 0° C., then added to a solution of (2-chloropyridin-4-yl)methanol and phenol in anhydrous tetrahydrofuran (50 mL) at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes then at ambient temperature for 16 hours. The reaction was quenched with saturated ammonium chloride solution (10 mL). The solvent was evaporated in vacuo. The residue was diluted with ethyl acetate (350 mL), washed with 1 N sodium hydroxide solution (3×40 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate/hexane (1/9) to afford 2-chloro-4-(phenoxymethyl)pyridine as a gummy solid in 61% yield (2.34 g): 1H NMR (300 MHz, CDCl3) δ 8.36 (d, J=5.1 Hz, 1H), 7.40 (s, 1H), 7.32-7.24 (m, 3H), 7.01-6.91 (m, 3H), 5.05 (s, 2H); MS (ES+) m/z 220.2 (M+1).

Provenance & Evidence