Sodium Iodide → 1-Iodoethyl ethyl carbonate

Participants

Reaction Conditions

Reaction Steps

1-Chloroethyl ethyl carbonate (5.0 g, 32.8 mmol) was dissolved in 125 mL acetonitrile. Sodium iodide (22.1 g, 147.5 mmol) was added and stirred at 60° C. for 1.5 hours. The reaction was evaporated, diluted with ether and filtered. The filtrate was evaporated to a dark red oil, to afford 1-iodoethyl ethyl carbonate (4.12 g, 51% yield). N016 (2.07 g, 11.3 mmol) and freshly made 1-iodoethyl ethyl carbonate (4.12 g, 16.9 mmol) were dissolved in 15 mL acetonitrile and stirred at room temperature overnight. The reaction was evaporated, diluted with ethyl acetate, washed with 0.2N Na2S2O3 and brine, dried over magnesium sulfate and evaporated. Chromatography was performed using 50% ethyl acetate/hexanes to yield a colorless oil (890 mg, 28% yield). 1H NMR (400 MHz, d-DMSO) δ 6.28 (dq, J=2.6, 5.6 Hz, 1H), 4.76 (dt, J=2.9, 5.7 Hz, 1H), 4.12 (q, J=7.1 Hz, 2H), 3.97-3.86 (m, 1H), 3.55-3.31 (m, 4H), 1.96-1.77 (m, 4H), 1.47 (d, J=5.5 Hz, 3H), 1.17 (dt, J=18.4, 7.1 Hz, 3H). LC tr=2.98 minutes (C-18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23° C.). ES(pos)MS m/z 300 (M+Na calcd for C10H19N3O6 requires 300).

Provenance & Evidence