Tetrahydrofuran → 5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1-hydroxy-2,2-dimethoxy-1-methylethyl)-1,3-thiazol-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 (1.00 g), 5-(1-hydroxy-2,2-dimethoxy-1-methylethyl)-1,3-thiazole-2-carbaldehyde (0.73 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (77 mg), triethylamine (0.16 mL), tetrahydrofuran (8 mL) and ethanol (8 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 (1.14 g, yield 69%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio). MS: 580 (MH+).

Provenance & Evidence