Acetone Cyanohydrin → 4-hydroxy-5-[(3-methoxyphenyl)methyl]-2-phenethyl-2-phenyl-3H-pyran-6-one

Participants

Reaction Steps

The title compound was prepared as described in General Method 8 using the following: 5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (0.300 g, 1.02 mmol), Et3N (0.15 mL, 1.1 mmol), 2-methoxybenzoyl chloride (0.17 g, 1.02 mmol), CH2Cl2 (4.0 mL), acetonitrile (4.0 mL), acetone cyanohydrin (0.05 mL, 0.5 mmol), Et3N (0.35 mL, 2.5 mmol), glacial acetic acid (5.0 mL), sodium cyanoborohydride (0.47 g, 7.5 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 1% MeOH in CH2Cl2) to provide a solid (0.227 g, 62°-64° C.). 1H NMR (400 MHz, DMSO-d6) δ10.823 (bs, 1H), 7.436-7.362 (m, 5H), 7.265 (t, 2H, 7.176-7.098 (m, 3H), 7.022 (td, 1H, J=1 Hz, J=8 Hz), 6.815 (d, 1H, J=7.5 Hz), 6.400 (td, 1H, J=1 Hz, J=7.5 Hz), 5.952 (dd, 1H, J=1 Hz, J=7 Hz), 3.716 (s, 3H), 3.391-3.169 (m, 4H), 2.650-2.582 (m, 1H), 2.354-2.182 (m, 3H).

Provenance & Evidence