Ethanol → 5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-1-(pyridin-2-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one (200 mg) in a mixed solvent of ethanol (3 mL) and tetrahydrofuran (3 mL) were added pyridine-2-carbaldehyde (71.0 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (16.0 mg) and triethylamine (33 μL), and the mixture was stirred under argon atmosphere at 80° C. 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 69%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 470 (MH+).

Provenance & Evidence