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) δ 10.922 (bs, 1 H), 7.395-7.315 (m, 5 H), 7.297-7.126 (m, 3 H), 7.084-7.028 (m, 5 H), 6.775-6.611 (m, 2 H), 3.423 (s, 2 H), 3.248 (d, 1 H, J=17 Hz), 3.175 (d, 1 H, J=17 Hz), 2.619-2.551 (m, 1 H), 2.292-2.227 (m, 3 H).

Provenance & Evidence