m-Chloroperbenzoic acid → HCID 86650542, compound

Participants

Reaction Steps

Epoxidation of alkene 121 with 3-chloroperbenzoic acid as in Example 2G, followed by chromatography of the product on silica gel, eluting with 0-15% CH2Cl2/petroleum ether (foreruns) and then with 15-75% CH2Cl2/petroleum ether and CH2Cl2, gave 2-methyl-2-({[4-(trifluoromethoxy)benzyl]oxy}methyl)oxirane (123) (93%) as an oil; 1H NMR (CDCl3) δ 7.37 (dt, J=8.7, 2.4 Hz, 2H), 7.19 (br d, J=7.9 Hz, 2H), 4.59 (d, J=12.1 Hz, 1H), 4.54 (d, J=12.1 Hz, 1H), 3.61 (d, J=11.1 Hz, 1H), 3.44 (d, J=11.1 Hz, 1H), 2.75 (d, J=4.9 Hz, 1H), 2.64 (d, J=4.9 Hz, 1H), 1.40 (s, 3H); HRCIMS (NH3) calcd for C12H17F3O3N m/z [M+H+NH3]+ 280.1161. found 280.1144.

Provenance & Evidence