Triethylamine → 1-[4-({[tert-butyl(diphenyl)silyl]oxy}methyl)pyridin-2-yl]-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Participants

Reaction Steps

To a solution of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (1.00 g) in ethanol (15 mL) were added 4-({[tert-butyl(diphenyl)silyl]oxy}methyl)pyridine-2-carbaldehyde (1.40 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (95.0 mg) and triethylamine (190 μL), and the mixture was stirred with heating under reflux for 4 hr under argon atmosphere. 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 (1.90 g, yield 88%) was obtained as a brown oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 698 (MH+).

Provenance & Evidence