m-Chloroperbenzoic acid → HCID 86650547, compound

Participants

Reaction Steps

Epoxidation of alkene 139 with 3-chloroperbenzoic acid as in Example 2G for 4 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 0-5% EtOAc/CH2Cl2, gave 2-chloro-1-[2-(2-methyl-2-oxiranyl)ethyl]-4-nitro-1H-imidazole (140) (88%) as a cream solid: mp (CH2Cl2/pentane) 82-85° C.; 1H NMR (CDCl3) δ 7.78 (s, 1H), 4.12 (t, J=7.6 Hz, 1H), 2.66 (d, J=4.4 Hz, 1H), 2.62 (d, J=4.4 Hz, 1H), 2.19 (dt, J=14.3, 7.7 Hz, 1H), 2.04 (dt, J=14.3, 7.4 Hz, 1H), 1.39 (s, 3H); HRFABMS calcd for C8H11ClN3O3 m/z [M+H]+ 234.0459, 232.0489. found 234.0466, 232.0488.

Provenance & Evidence