Ethanol → HCID 13463001, compound

Participants

Reaction Steps

To a solution of 1.70 g of 3-chloro-2-naphthoic acid (8.23 mmol) in 50 mL of 1,4-dioxane is added 2.3 mL of triethylamine (16.45 mmol) followed by 2.7 mL of DPPA (12.34 mmol). The mixture is stirred for 2 hours at room temperature under an atmosphere of nitrogen. Then 4.8 mL (82.3 mmol) of EtOH is added and the reaction is heated to reflux and stirred for an additional 2 hours. The solvents are evaporated in vacuo and the remaining residue is dissolved in 50 mL of EtOAc and washed with 20 mL of 5% aqueous citric acid, 20 mL of 5% Na2CO3 and dried over MgSO4. The solvents are evaporated to give a residue that is purified by flash chromatography on silica gel (50% CH2Cl2/hexane) to give N-(3-chloro-2-naphthyl)carbamic acid ethyl ester as a yellow oil.

Provenance & Evidence