Ethyl Acetate → 1-(3-Iodophenoxy)-3,6,9-trioxadecane

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[(methanesulfonyl)-oxy]-3,6,9-trioxadecane (11.6 g, 47.9 mmol) in dry DMF (145 ml) was added 3-iodophenol (10.6 g, 48.2 mmol) and potassium carbonate (6.6 g, 47.8 mmol). The reaction was immersed in an oil bath which was warmed to 68° C. over a period of 0.5 hr. The reaction was stirred at this temperature under an N2 atmosphere for 16 hrs and then at 82° C. for an additional 2 hrs. At the end of this period, the reaction was cooled, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into ethyl acetate (500 ml), washed with water (200 ml), 1 N aqueous sodium hydroxide (200 ml) and brine (200 ml), dried (Na2SO4), filtered and evaporated in vacuo to provide a light brown oil. Flash column chromatography (silica, 1:3 to 1:2; EtOAc:hexane) provided 1-(3-iodophenoxy)-3,6,9-trioxadecane as a light yellow oil (10.8 g, 37.1%). Title Compound: 1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired product. Calculated for C13H10O4I:C,42.52; H, 5.49; I, 34.56. Found: C, 42.50, H, 5.13; I, 34.78.

Provenance & Evidence