反应详情

温度

-78 °C

Diisobutylaluminum hydride (0.35 ml of a 1.76 M solution in toluene, 0.61 mmole) was added dropwise to a stirred -78° C. solution of (trans)-3-[3-(6-phenyl-1,3,5-hexatriynyl)oxiranyl]-2-propenal (50 mg, 0.20 mmole; see Example 5) in 6 ml of dry tetrahydrofuran. The mixture was stirred for 2 hours at -78° C. and was then quenched at that temperature by the dropwise addition of ca. 0.5 ml of a solution of methanol-acetic acid 4:1. The mixture was warmed to room temperature, water was added and the mixture was extracted with ether. The combined ether extracts were washed with water and saturated aqueous sodium chloride and were dried over anhydrous magnesium sulfate. Removal of solvent gave an oil which was purified by preparative thin layer chromatography (ethyl acetate-hexane 1:1) to afford 34 mg pure title compound, melting point 65°-66° C.

1. customwas then quenched at that temperature by the dropwise addition of ca. 0.5 ml of a solution of methanol-acetic acid 4:1
2. temperatureThe mixture was warmed to room temperature
3. additionwater was added
4. extractionthe mixture was extracted with ether
5. washThe combined ether extracts were washed with water and saturated aqueous sodium chloride
6. dry with materialwere dried over anhydrous magnesium sulfate
7. customRemoval of solvent
8. customgave an oil which
9. customwas purified by preparative thin layer chromatography (ethyl acetate-hexane 1:1)