Acetone Cyanohydrin → 5,6-Dihydro-4-hydroxy-3-[(3-methylphenyl)methyl]-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

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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 (0.250 g, 0.850 mmol), Et3N (0.12 mL, 0.85 mmol), 3-methylbenzoyl chloride (0.12 mL, 0.89 mmol), CH2Cl2 (3.0 mL), acetonitrile (5.0 mL), acetone cyanohydrin (0.037 mL, 0.40 mmol), Et3N (0.24 mL, 1.8 mmol), glacial acetic acid (5.0 mL), sodium cyanoborohydride (0.16 g, 2.6 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 2% MeOH in CH2Cl2) to provide a solid (0.250 g, m.p. 53°-55° C.). 1H NMR (400 MHz, DMSO-d6) δ 10.884 (bs, 1 H), 7.418-7.310 (m, 5 H), 7.231 (t, 2 H, J=7.5 Hz), 7.148-7.122 (m, 1 H), 7.071 (d, 2 H, J=7 Hz), 6.929 (t, 1 H, J=7.5 Hz), 6.843 (d, 1 H, J=7.5 Hz), 6.587 (d, 1 H, J=7.5 Hz), 6.545 (s, 1 H), 3.398 (AB, 2 H, JAB =15.5 Hz), 3.248 (d, 1 H, J=17 Hz), 3.125 (d, 1 H, J=17 Hz), 2.607-2.511 (m, 1 H), 2.338-2.159 (m, 3 H), 2.094 (s, 3 H).

Provenance & Evidence