Sodium Iodide → HCID 178453921, compound

Participants

Reaction Steps

Bromide 17 (1.1 g, 3.6 mmol), cesium carbonate (1.47 g, 4.5 mmol), and sodium iodide (0.68 g, 4.5 mmol) were added to a solution of compound 19 (0.63 g, 3.0 mmol) in acetonitrile (40 mL). After refluxing for 48 hours, the mixture was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, and dried over anhydrous sodium sulfate (Na2SO4). Flash column chromatography (MeOH/EtOAc, 1:6) gave compound 20 as a colorless oil (0.8 g, 61%). 1H NMR (CDCl3, 300 MHz) δ 4.93 (s, 2H), 4.02 (d, J=7.4 Hz, 1H), 3.50-3.30 (m, 1H), 3.10-2.95 (m, 1H), 2.80-2.35 (m, 8H), 2.05-1.90 (m, 3H), 1.85-1.60 (m, 3H), 1.55-1.00 (m, 9H), 1.44 (s, 9H), 0.87 (t, J=7.2 Hz, 3H).

Provenance & Evidence