m-Chloroperbenzoic acid → HCID 68864539, compound

Participants

Reaction Steps

A mixture of Example 132A (170 mg, 0.43 mmol) in CH2Cl2 (5 mL) at 0° C. was treated with mCPBA (136 mg, 0.47 mmol), warmed to room temperature, stirred for 2 hours, diluted with ethyl acetate, washed with NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was dissolved in toluene (5 mL), treated with activated-zinc iodide (37 mg, 0.12 mmol), heated to reflux for 1 hour, diluted with diethyl ether, washed with brine, dried (Na2SO4), filtered, and concentrated to provide the desired product (140 mg, 79% yield). MS (ESI) m/e 410 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.92 (s, 1H), 7.73 (m, 2H), 7.4 (m, 2H), 7.24 (d, 1H), 7.0 (d, 1H), 3.6 (q, 1H), 3.15 (m, 1H), 2.93 (m, 1H), 2.59 (m, 1H), 2.41 (m, 1H), 1.2 (d, 3H).

Provenance & Evidence