Triacetoxyperiodinane → 2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazole-5-carbaldehyde

Participants

Reaction Steps

A mixture of [2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanol (0.49 g), Dess-Martin reagent (0.50 g) and acetonitrile (10 mL) was stirred at room temperature overnight. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (0.46 g, yield 98%) was obtained as yellow crystals from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). melting point 175-176° C. MS: 471 (MH+).

Provenance & Evidence