反应详情

5-(4-octylphenyl)tetrahydrofuran-3-ol (1 g, 3.62 mmol) was dissolved in dichloromethane (36.2 ml) in a sealed vial. PCC (3.12 g, 14.47 mmol) (Aldrich) was added and the reaction stirred for about 16 h. The methylene chloride was evaporated and the residue stirred with ethyl acetate. The ethyl acetate was filtered through a pad of silica gel (approx. 50 mL silica) and product eluted with ethyl acetate. This removed most of the brown color. Concentrate and then chromatograph on a 40 g redi-sep column with 20-50% ethyl acetate in heptane. Remove solvent under reduced pressure to provide 5-(4-octylphenyl)dihydrofuran-3(2H)-one (0.839 g, 3.06 mmol, 85% yield) as a colorless oil: LC/MS (method A) Rt=4.14 min.; MS m/z: 275.25 (M+H)+.

1. customThe methylene chloride was evaporated
2. stirringthe residue stirred with ethyl acetate
3. filtrationThe ethyl acetate was filtered through a pad of silica gel (approx. 50 mL silica) and product
4. washeluted with ethyl acetate
5. customThis removed most of the brown color
6. concentrationConcentrate