3.13. Procedure for the Fleming-Tamao Oxidation of Silyl Tetrahydropyran 2d

Mercuric acetate (0.466 mmol, 1.5 eq) was added to a solution of 2d (0.311 mmol) in peracetic acid (35–40% solution in dilute acetic acid; 2 mL) and the mixture was stirred for 3 h at room temperature. Toluene (6 mL) was added and the mixture of solvents was evaporated under reduced pressure. The residue was taken up in ether, filtered and evaporated under reduced pressure. Purification by flash column chromatography (hexane/EtOAc, 3:1 to pure EtOAc) yielded 3d (0.186 mmol, 60%) as a white viscous liquid (melting point could not be measured). Rf = 0.4 (silica, hexane/EtOAc, 4:1).