N,N'-Dimethylethylenediamine → (S)-3-(4-iodophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A resealable tube was charged with (S)-5,5-dimethyl-4-phenyloxazolidin-2-one (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (1.01 g, 5.28 mmol), 1,4-diiodobenzene (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (3.48 g, 10.56 mmol), tribasic potassium phosphate (5.61 g, 26.4 mmol) and dioxane (20.0 mL). The mixture was purged with argon and then copper (I) iodide (1.006 g, 5.28 mmol) and N,N′-dimethylethylenediamine (1.137 mL, 10.56 mmol) were added. The system was purged with argon, the tube was sealed, and the reaction mixture was heated at 100° C. for 12 hours. The reaction mixture was filtered through Celite® brand filter aid and concentrated to afford a purple solid. This material was purified via column chromatography on silica gel (RediSep 80 g column, gradient elution with 0-25% EtOAc-hexane) to afford (S)-3-(4-iodophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (1.271 g, 3.23 mmol, 61.2% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=7.64-7.59 (m, 2H), 7.39-7.33 (m, 2H), 7.33-7.27 (m, 3H), 7.26-7.20 (m, 2H), 5.43 (s, 1H), 1.61 (s, 3H), 0.89 (s, 3H).

Provenance & Evidence