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

Participants

Reaction Steps

A mixture of 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.50 g), 5-[2-methoxy-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyridine-2-carbaldehyde (0.42 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (38 mg), triethylamine (0.1 mL), tetrahydrofuran (5 mL) and ethanol (5 mL) was stirred with heating under reflux for 2 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and the title compound (0.70 g, yield 79%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 614 (MH+).

Provenance & Evidence