Ethanol → 1-[5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Participants

Reaction Steps

To a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one (180 mg) in a mixed solvent of ethanol (3 mL) and tetrahydrofuran (3 mL) were added 5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridine-2-carbaldehyde (158 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (14.7 mg) and triethylamine (29.9 μL), and the mixture was stirred with heating under reflux under argon atmosphere for 3 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (180 mg, yield 58%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 628 (MH+).

Provenance & Evidence