反应详情

To a solution of 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (141 mg) in a mixed solvent of ethanol (1 mL) and tetrahydrofuran (1 mL) were added 5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazole-2-carbaldehyde (171 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (12.1 mg) and triethylamine (24.4 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 (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (168 mg, yield 57%) was obtained as white crystals from a fraction eluted with ethyl acetate-hexane (19:1, volume ratio).

1. temperaturewith heating
2. temperatureunder reflux for 3 hr
3. washwashed with water
4. dry with materialThe ethyl acetate layer was dried (MgSO4)
5. concentrationconcentrated