Ethanol → HCID 59331612, compound

Participants

Reaction Steps

To a solution of 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (500 mg) in a mixed solvent of ethanol (15 mL) and tetrahydrofuran (5 mL) were added ethyl glyoxylate (polymer type, 47% toluene solution) (623 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (43 mg) and triethylamine (86 μL), and the mixture was heated under reflux under argon atmosphere for 30% min. 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 dissolved in acetic acid (5 mL), ammonium acetate (1.7 g) was added, and the mixture was stirred at 110° C. for 30 min. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. 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 (210 mg, yield 34%) was obtained as a pale-yellow amorphous solid from a fraction eluted with hexane-ethyl acetate (1:1, volume ratio). MS: 432 (MH+).

Provenance & Evidence