Ethanol → HCID 59331402, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (350 mg), ethyl glyoxylate (polymer type, 47% toluene solution) (260 mg), triethylamine (0.31 mL), ethanol (15 mL) and tetrahydrofuran (5 mL) was added 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (280 mg) and the mixture was heated under reflux for 1 hr under argon atmosphere. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. A mixture of the obtained residue, ammonium acetate (1.36 g) and acetic acid (10 mL) was stirred at 120° C. for 2 hr. The reaction mixture was concentrated, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. 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 (140 mg, yield 31%) was obtained as a pale-brown oil from a fraction eluted with hexane-ethyl acetate (1:1-1:2, volume ratio). MS: 406 (MH+).

Provenance & Evidence