Ethanol → HCID 68802648, compound

Participants

Reaction Steps

To a suspension of 6-hydroxy-2-naphthoic acid (5 g, 26.6 mmol) and triethylamine (7.39 mL, 53.1 mmol) in 1,4-dioxane (50 mL) at room temperature, is added DPPA (8.59 mL, 39.9 mmol). After stirring at room temperature for 2.5 hours, ethanol (15.5 mL, 266 mmol) is added and the reaction is heated to reflux temperature overnight. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator to give an oil. Flash chromatography on silica gel (5% methanol in dichloromethane) gives N-(6-hydroxy-2-naphthyl)carbamic acid ethyl ester as a white solid.

Provenance & Evidence