Tetrahydrofuran → 1-{5-[2-methoxy-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyridin-2-yl}-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

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Reaction Steps

A mixture of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (1.07 g), 5-[2-methoxy-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyridine-2-carbaldehyde (0.97 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (90 mg), triethylamine (0.23 mL), tetrahydrofuran (8 mL) and ethanol (8 mL) was stirred with heating under reflux for 1 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and the title compound (1.05 g, yield 54%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 588 (MH+).

Provenance & Evidence