Ethanol → HCID 59331602, compound

Participants

Reaction Steps

To a solution of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydrofuran-2-yl)pent-1-en-3-one (930 mg) in a mixed solvent of ethanol (7.5 mL) and tetrahydrofuran (7.5 mL) were added pyridine-2-carbaldehyde (323 μL), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (89.6 mg) and triethylamine (181 μL), and the mixture was stirred with heating under reflux 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 dried (MgSO9) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (302 mg, yield 24%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (19:1, volume ratio). MS: 416 (MH+).

Provenance & Evidence