2-Cyclohexen-1-one → HCID 24794625, compound

Participants

Reaction Conditions

Reaction Steps

In a dry sealed tube under N2 were placed N-(2-phenylethylidene)methylamine N-oxide (2.0 g, 13.4 mmol) and 2-cyclohexenone (5 ml). The reagents were stirred at 100° C. for 15 hours. Unreacted 2-cyclohexenone was removed by Kugelrohr distillation to yield the crude product as a viscous brown oil (K100%). The crude product was purified by flash chromatography on silica gel (Sorbsil C60, 60A) using 60:40 v/v petroleum ether (fraction of bp 40°-60° C.):ethyl acetate as the solvent system to give the unsubstituted title compound as an orange oil (2.48 g. 75%), νmax (film) 2944, 2872, 1709, 1455, 1238 cm-1 ; δH (250 MHz, CDCl3 --Me4Si) 1.75-1.95 (4H, br m), 2.20-2.40 (2H, br m), 2.50 (3H, s), 3.70-3.80 (1H, t), 2.85-2.95 (2H, t), 3.45-3.55 (1H, br m), 4.30-4.40 (1H, br m), 7.15-7.30 (5H, br m), M/z 246 (MH+ 100%) (Found: MH+ 246.149; C15H19NO2 requires MH+ 246.1522).

Provenance & Evidence