Triethylamine → HCID 59331321, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[4-(cyclopropylsulfonyl)phenyl]-5-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]pent-1-en-3-one (1.70 g) in ethanol (10 mL) were added 1,3-thiazole-2-carbaldehyde (0.33 mL), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (93 mg) and triethylamine (0.19 mL), and the mixture was heated under reflux for 12 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. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-60:40, volume ratio) to give a colorless oil. To a solution of the obtained oil in N,N-dimethylformamide (20 mL) was added ammonium acetate (820 mg), and the mixture was stirred at 100° C. for 1.5 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=10:90-80:20, volume ratio) to give the title compound (0.100 g, yield 5%) as a colorless oil. MS: 637 (MH+).

Provenance & Evidence