Ethanol → HCID 59331403, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (1.79 g) in a mixed solvent of ethanol (30 mL) and tetrahydrofuran (30 mL) was deaerated, and 5-(1,2-dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde (1.52 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (150 mg) and triethylamine (0.310 mL) were added. The reaction solution was purged with nitrogen, and the mixture was stirred at 70° C. for 1.5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the residue in acetic acid (150 mL) was added ammonium acetate (4.28 g), and the mixture was stirred at 110° C. for 2 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-100:0, volume ratio) to give the title compound (1.79 g, yield 65%) as a colorless amorphous solid. MS: 499 (MH+).

Provenance & Evidence