3,4-dihydro-2H-pyran → (E)-N-(3-methyl-4-(3-(3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acryloyl)-phenyl)acetamide

Participants

Reaction Steps

To a solution of (E)-N-(4-(3-(4-hydroxy-3-methylphenyl)acryloyl)-3-methylphenyl)acetamide (100 mg, 0.32 mmol) in DCM was added 300 mg of H2SO4/SiO2 (cat. amount), and 3,4-dihydro-2H-pyran (500 mg, 5.9 mmol). The reaction mixture was stirred for 1 h at room temperature. The resulting slurry was filtered, concentrated under reduced pressure, and the product was purified by column chromatography (EtOAc/Hex, 10% to 50% gradient), resulting in 80 mg (78%) of the title compound. MS (EI) for C24H27NO4: 394 (MH+).

Provenance & Evidence