Hexane → HCID 58902326, compound

Participants

Reaction Steps

To a solution of 7-{[2-(tert-butoxycarbonyl)pyridin-4-yl]oxy}-2-naphthoic acid (5.25 g, 14.3 mmol) in MeOH (50 mL) and toluene (50 mL), was added a solution of 2.0M trimethylsilyldiazomethane in hexane (14.3 mL, 28.7 mmol) dropwise. The reaction was allowed to stir for 5 h, after which time 2.0M trimethylsilyldiazomethane in hexane (7.17 mL, 14.3 mmol) was added. Stirring continued for an additional 1 h. The solvents were evaporated and the residue was dissolved in EtOAc and washed with saturated NaHCO3 and brine. The organic solution was dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography to give tert-butyl 4-{[7-(methoxycarbonyl)-2-naphthyl]oxy}pyridine-2-carboxylate as an off-white solid (3.18 g, 58.4%). LCMS: (FA) ES+ 380.2.

Provenance & Evidence