Monobenzone → HCID 66956632, compound

Participants

Reaction Steps

Reaction of epoxide 140 (see Example 2JJ) with 4-(benzyloxy)phenol as in Example 2AA at 82° C. for 10 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 2% EtOAc/CH2Cl2, gave 1-[4-(benzyloxy)phenoxy]-4-(2-chloro-4-nitro-1H-imidazol-1-yl)-2-methyl-2-butanol (142) (79%) as an oil; 1H NMR (CDCl3) δ 7.79 (s, 1H), 7.44-7.29 (m, 5H), 6.92 (dt, J=9.2, 3.0 Hz, 2H), 6.83 (dt, J=9.2, 3.0 Hz, 2H), 4.28 (ddd, J=14.0, 9.7, 6.1 Hz, 1H), 4.23 (ddd, J=14.0, 9.7, 6.3 Hz, 1H), 3.81 (d, J=9.1 Hz, 1H), 3.77 (d, J=9.0 Hz, 1H), 2.29 (s, 1H), 2.22 (ddd, J=13.8, 9.6, 6.2 Hz, 1H), 2.02 (ddd, J=13.6, 9.7, 6.5 Hz, 1H), 1.38 (s, 3H); HRESIMS calcd for C21H23ClN3O5 m/z [M+H]+ 434.1293, 432.1321. found 434.1298, 432.1319.

Provenance & Evidence