m-Chloroperbenzoic acid → HCID 86593508, compound

Participants

Reaction Steps

To a solution of amine 34 (42 mg, 0.14 mmol) in CH2Cl2 (2 mL) was added 140 mg of m-CPBA (0.57 mmol based on 70% content). The mixture was stirred at room temperature for 30 min, then aqueous NaHSO3 was added, the resulting two layers were separated, and the aqueous phase was extracted with CH2Cl2 (3×3 mL). The combined organic layers were washed with saturated aqueous Na2CO3, dried with Na2SO4, and concentrated. The residue was purified by flash column chromatography (EtOAc/hexanes; 1:2) to afford 36 mg (91%) of trienyl sulfone 35. 1H NMR (CDCl3, 300 MHz) δ 7.88-7.92 (m, 2H), 7.54-7.67 (m, 3H), 7.51 (s, 1H), 6.24 (dt, J=11.4 Hz, 1.2 Hz, 1H), 5.90 (dd, J=11.4 Hz, 5.4 Hz, 1H), 5.78 (s, 1H), 5.72(s, 1H), 4.36 (s, 1H), 2.64 (m, 1H), 1.81 (br s, 1H), 1.11 (d, J=7.5 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ 145.6, 140.2, 139.3, 137.0, 136.1, 133.6, 129.5, 128.1, 128.0, 120.2, 75.1, 39.3, 16.4.

Provenance & Evidence