反应详情

温度

85 °C

A degassed solution of dialkene (114)(1.83 g, 3.93 mmol) in dichloroethane (1.8 L, stored over 4 Å molecular sieves before use) was added Howeyda-Grubbs 1st generation catalyst (0.165 g, 0.27 mmol), then shortly degassed and stirred at approximately 85° C. bath temperature overnight (monitored by LC-MS). The reaction mixture was then allowed to cool somewhat after which solid phase catalyst scavenger (1.3 g, MP-TMT, Argonaut Technologies) and stirred additional 1.5 h, then filtered and concentrated. Flash chromatography of the residue (YMC-GEL silica) using stepwise gradient elution (ethyl acetate in hexane, 50-100%) and concentration of the appropriate fractions gave the title compound as a brown syrup which crystallized upon standing (1.33 g, 77%, purity approx. 90%). This material was crystallized from 4:1 ethyl acetate (40 ml) giving a brown solid (0.79 g, 1.8 mmol) and chromatography of the mother liqure gave additional product (0.36 g, 0.81 mmol). LR-MS: Calcd for C23H37N2O6: 437. Found: 437 [M+H].

1. customshortly degassed
2. temperatureto cool somewhat after which solid phase catalyst scavenger (1.3 g, MP-TMT, Argonaut Technologies)
3. stirringstirred additional 1.5 h
4. filtrationfiltered
5. concentrationconcentrated
6. washelution (ethyl acetate in hexane, 50-100%) and concentration of the appropriate fractions