tert-Butanol → tert-Butyl (6-methoxynaphthalen-2-yl)carbamate

Participants

Reaction Steps

A mixture of 6-methoxy-naphthalene-2-carboxylic acid (10.00 g, 49.5 mmol), triethylamine (6.9 mL, 49.5 mmol) and diphenylphosphoryl azide (10.7 mL, 49.6 mmol) in 200 mL of anhydrous tert-butyl alcohol was refluxed under nitrogen for 5.5 h. The tert-butyl alcohol was removed under reduced pressure. The residue was dissolved in methylene chloride and extracted with 1 N HCl, 1 N NaOH, dried (MgSO4) and the solvent removed under reduced pressure to give (6-Methoxy-naphthalen-2-yl)-carbamic acid tert-butyl ester (11.14 g, 82%) as an off-white solid, mp 124-127° C.

Provenance & Evidence