Potassium Iodide → HCID 19070827, compound

Participants

Reaction Steps

To a solution of 3-aminophenol (2.18 g, 20 mmol) in tetrahydrofuran (10 ml) is added di-tert-butyl dicarbonate (4.578 g, 21 mmol) and the mixture is stirred for 15 hr at room temperature. To the residue obtained by concentrating the reaction mixture is purified by chromatography on silica gel (hexane/ethyl acetate (5:1)). To a solution of the resultant oily residue of 3-(N-tert-butyloxycarbonylamino)phenol in dimethylformamide are added ethyl 2-bromoacetate (2.44 ml, 22 mmol), potassium iodide (183 mg, 1.1 mmol) and potassium carbonate (3.04 g, 22 mmol) and the mixture is stirred for 15 hr at room temperature. The reaction mixture is concentrated under reduced pressure and the concentrate is partitioned between a mixture of ethyl acetate and water. The organic layer is dried over magnesium sulfate and concentrated under reduced pressure. The resultant crude product is purified by chromatography on silica gel (toluene/ethyl acetate (9:1)) to give the titled compound as colorless oil.

Provenance & Evidence