Tetrahydrofuran → HCID 54223603, compound

Participants

Reaction Steps

To a solution of the silylether prepared in 1N (237 mg, 0.43 mmole) in tetrahydrofuran (5 ml) was added tetra-n-butylammonium fluoride trihydrate (205 mg, 0.65 mmole). The mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure. The residue was dissolved in methylene chloride, washed with water and dried over sodium sulfate. Filtration and concentration under reduced pressure afforded an oil. Flash chromatography on silicagel and elution with a 15:95 mixture of ethyl-acetate and benzene afforded the expected alcohol as an oil (119 mg, 88%). NMR (H1, CDCl3, 360 MHz) characteristic peaks: 2.32 (dm, JHF =21.6 Hz, 2), 2.72 (t, JHH =7 HZ, 2), 3.73 (m, 2), 5.09 (dt, JHF =21.6 Hz, JHH =8 Hz, 1), 5.39 (m, 4).

Provenance & Evidence