Ozone → HCID 57190765, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 34 g (0.16 mmole) of the crude (3S,5S)-3-(3-hydroxypropyl)-5-(1-methylethenyl)-2-methylcyclohexanone in 600 ml of MeOH at -78° C. was bubbled with ozone until the blue color persisted. Excess ozone was removed by flushing the solution with argon. The reaction mixture was warmed up to -20° C., added with 64.8 g (0.32 mole) of cupric acetate and stirred for 15 minutes. This was then added with 54.2 g (0.195 mole) of ferrous sulfate heptahydrate in small portions. After the addition, the reaction mixture was stirred at -20° C. for 3 hours, room temperature for 1 hr, quenched with 650 ml of water and extracted with 3×1000 ml ether. The aqeous layer was then acidified with 6N HCl until it became homogeneous and extracted with 2×800 ml of ether. The combined etheral extracts were washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated to give 18.5 g of the crude (5S)-5-(3-hydroxypropyl)-6-methyl-2-cyclohexene-1-one which was used as such for the next step. An analytical sample of the conjugated enone was obtained by further purification of the crude (3S,5S)-3-(3-hydroxypropyl)-5-(1-methylethenyl)-2-methylcyclo-hexanone on a silica gel column (2:1, hexane/EtOAc). IR (CHCl3): 1670, 3625 cm-1. 1H NMR (200 MHz): δ1.04 (d, J=7.3 Hz, 1.5H), 1.17 (d, J=6.9 Hz, 1.5H), 1.43-1.65 (m, 4H), 1.90 (m, 1HO, 2.10-2.27 (m, 2H), 2.34-2.42 (md, 1H), 2.49-2.57 (m, 1H), 3.65 (t, J=6.4 Hz, 2H), 5.98 (mt, 1H), 6.89-6.92 (m, 1H). Mass spectrum m/e: M+ (168). Anal. for C10H16O2 : Calc. for C, 71.39; H, 9.59. Found: C, 71.34; H, 9.55.

Provenance & Evidence