Hydrogen Peroxide → HCID 13075706, compound

Participants

Reaction Steps

To a solution of 27 ml of NaOH and 1 ml of 30% H2O2 in degassed MeOH (20 ml) was added a THF solution (10 ml) of 497 mg of the trienone (3) and then the reaction mixture was stirred for 20 hr at room temperature. The reaction mixture was diluted with brine and extracted with ether. The etheral extract was submitted to silica gel column chromatography (AcOEt-n-hexane, 1:4) to give 499 mg (97%) of the epoxide (4): mp 181°-184° C. (from AcOEt-cyclohexane), MS m/e 520(M+), 505, 503; NMR(CDCl3)δ0.70(s, 18-H3), 0.95(d, J=6 Hz, 21-H3), 1.00(s, 19-H3), 3.45 (1H, m, 2-H), 3.62(1H, d, J=6 Hz, 1-H), 4.10(1H, s, OH), 5.62(1H, bs, 4 -H), 6.04(2H, s, 6- and 7-H).

Provenance & Evidence