Tetrahydrofuran → 5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)-1-[5-(2,2,2-trifluoro-1-hydroxyethyl)-1,3-thiazol-2-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 (0.30 g), 5-(2,2,2-trifluoro-1-hydroxyethyl)-1,3-thiazole-2-carbaldehyde (0.20 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (23 mg), triethylamine (0.05 mL), tetrahydrofuran (4 mL) and ethanol (2 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 (0.45 g, yield 90%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 560 (MH+).

Provenance & Evidence