反应详情

To a solution of alcohol 6 (230 mg, 0.88 mmol) in CH2Cl2 (8 mL) was added 1-pentadecene (741 mg, 3.52 mmol). The solution was degassed twice using N2 (2×10 min). To the reaction mixture was added benzylidene[1,3-bis(2,4,6-trimethyl -phenyl)-2-imidazolidinylidene]dichloro-(tricyclohexylphosphine)ruthenium catalyst (22.4 mg, 0.026 mmol) at rt under N2. After the reaction mixture was stirred for 4 h under reflux, the solvent was removed and the product was purified by chromatography (hexane/EtOAc 4:1) to afford 7 (280 mg, 72%): Rf0.45 (EtOAc/hexane 1:3); 1H NMR (CDCl3) δ 0.88 (t, 3H, J=7.0 Hz), 1.25 (m, 24H), 1.44 (m, 9H), 2.06 (q, 2H, J=7.7 Hz), 2.89 (d, 1H, J=5.2 Hz), 3.38 (s, 3H), 3.67 (m, 2H), 3.94 (dt, 1H, J=3.2, 11.1 Hz), 4.22 (dd, 1H, J=5.0, 7.6 Hz), 4.53 (d, 1H, J=6.6 Hz), 4.67 (d, 1H, J=6.6 Hz), 5.26 (d, 1H,J =7.6 Hz), 5.36 (dd, 1H, J=8.0, 15.4 Hz), 5.75 (dt, 1H, J=6.6, 14.6 Hz); 13C NMR (CDCl3) δ 14.1, 22.7, 28.4, 29.0, 29.1, 29.3, 29.4, 29.6, 29.7, 31.9, 32.3, 54.9, 55.6, 62.3, 76.1, 78.3, 79.4, 93.8, 125.9, 136.9, 155.9; ESI-HRMS [M+Na]+C25H49NO5Na calcd for m/z 466.3508, found 466.3514.

1. customThe solution was degassed twice using N2 (2×10 min)
2. temperatureunder reflux
3. customthe solvent was removed
4. customthe product was purified by chromatography (hexane/EtOAc 4:1)