Sodium Chloride → HCID 68541861, compound

Participants

Reaction Conditions

Reaction Steps

Combine NaOtBu (3.6 g, 4 equiv.), THF (10 mL), and NMP (10 mL) in a round bottomed flask. Place under nitrogen and cool to 0° C. Dissolve 1-(3-iodo-phenyl)-propan-1-one (2 g, 9.4 mmol) in THF (10 mL) and add dropwise to the reaction. Immediately following, add methyl iodide (2.3 mL, 4 equiv.) via syringe. Stir at 0° C. for 5 hours. Quench reaction with water then dilute with ethyl acetate. Wash organics with water then aqueous saturated sodium chloride. Dry over magnesium sulfate, filter and concentrate in vacuo. Purify by silica chromatography (Hex→5% EtOAc:Hexanes) to give 2.0 g clear liquid. 1H NMR (400 MHz, DMSO-d6) δ 7.70 (m, 2H), 7.66 (m, 1H), 7.40 (m, 1H), 1.23 (s, 9H).

Provenance & Evidence