m-Chloroperbenzoic acid → HCID 86650543, compound

Participants

Reaction Steps

Epoxidation of alkene 122 with 3-chloroperbenzoic acid as in Example 2G for 2.5 h, followed by chromatography of the product on silica gel, eluting with 50% CH2Cl2/petroleum ether (foreruns) and then with 50-80% CH2Cl2/petroleum ether and CH2Cl2, gave 2-({[4-(benzyloxy)benzyl]oxy}methyl)-2-methyloxirane (124) (95%) as an oil: 1H NMR (CDCl3) δ 7.45-7.29 (m, 5H), 7.26 (dt, J=8.7, 2.4 Hz, 2H), 6.95 (dt, J=8.7, 2.5 Hz, 2H), 5.07 (s, 2H), 4.52 (d, J=11.6 Hz, 1H), 4.47 (d, J=11.6 Hz, 1H), 3.54 (d, J=11.0 Hz, 1H), 3.42 (d, J=11.0 Hz, 1H), 2.73 (d, J=4.9 Hz, 1H), 2.62 (d, J=4.9 Hz, 1H), 1.39 (s, 3H); HREIMS calcd for C18H20O3 m/z (M+) 284.1412. found 284.1416.

Provenance & Evidence