Tetrahydrofuran → 5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-[(2-methoxyethoxy)methyl]-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

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Reaction Steps

A mixture of 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.43 g), 5-[(2-methoxyethoxy)methyl]-1,3-thiazole-2-carbaldehyde (0.26 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (32 mg), triethylamine (0.07 mL), tetrahydrofuran (4 mL) and ethanol (4 mL) was stirred with heating under reflux for 2 hr. The reaction mixture was concentrated, and the residue was subjected to basic silica gel column chromatography, and the title compound (0.52 g, yield 79%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 550 (MH+).

Provenance & Evidence