反应详情

温度

50 °C

4-(4-octylphenyl)butane-1,2,4-triol (12 g, 40.6 mmol) was dissolved in 1,2-Dichloroethane (815 ml) under nitrogen. p-Toluenesulfonic acid monohydrate (1.55 g, 8.2 mmol) (TCI) was added and the reaction heated at about 50° C. for about 3 h. TLC in 1:1 EtOAc/heptane showed (PMA visualization) reaction complete. The solution was washed with saturated sodium bicarbonate and extract with methylene chloride (2×). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to a yellow oil. The resulting oil was chromatographed on 330 g redi-sep column eluting with 20% EtOAc in heptane for 10 min ramping to 50% over 20 min and then holding at 50% until all the product was off (monitor at 223 nm due to weak chromaphore at longer wavelengths). Removed solvent under reduced pressure to provide 5-(4-octylphenyl)tetrahydrofuran-3-ol (7.36 g, 26.6 mmol, 73.3% yield) as a colorless oil: LC/MS (method A) Rt=3.76 min.; MS m/z: 277.15 (M+H)+.

1. custom(PMA visualization) reaction complete
2. washThe solution was washed with saturated sodium bicarbonate
3. extractionextract with methylene chloride (2×)
4. washThe combined extracts were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated to a yellow oil
8. customThe resulting oil was chromatographed on 330 g redi-sep column
9. washeluting with 20% EtOAc in heptane for 10 min