Acetone Cyanohydrin → 5,6-Dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-3-phenylmethyl-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 (0.26 mL, 1.94 mmol), benzoyl chloride (0.109 mL, 0.94 mmol), CH2Cl2 (2.0 mL), acetonitrile (5.0 mL), acetone cyanohydrin (0.04 mL, 0.43 mmol), Et3N (0.26 mL, 1.9 mmol), glacial acetic acid (10.0 mL), sodium cyanoborohydride (0.151 g, 2.4 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 2% MeOH in CH2 Cl2) to provide a thick oil (0.384 g). 1H NMR (400 MHz, DMSO-d6) δ10.922 (bs, 1H), 7.395-7.315 (m, 5H), 7.297-7.126 (m, 3H), 7.084-7.028 (m, 5H), 6.775-6.611 (m, 2H), 3.423 (s, 2H), 3.248 (d, 1H, J=17 Hz), 3.175 (d, 1H, J=17 Hz), 2.619-2.551 (m, 1H), 2.292-2.227 (m, 3H).

Provenance & Evidence