tert-Butanol → HCID 86731411, compound

Participants

Reaction Steps

To a solution of 2-(benzyloxy)-5-(methoxymethoxy)isonicotinic acid (9.20 g) in tert-butyl alcohol (30 mL) were added diphenylphosphoryl azide (26.3 mL) and N,N-diisopropylethylamine (13.3 mL), and the mixture was stirred at room temperature for 1 hr, and then with refluxing at 80° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (11.4 g).

Provenance & Evidence