Acetone Cyanohydrin → HCID 178519060, compound

Participants

Reaction Steps

The desired compounds were prepared by adding 5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one (0.500 g, 1.88 mmol) and dry dichloromethane (10.0 mL) to a reaction vessel followed by the addition of the benzoyl chloride (0.22 mL, 1.88 mmol) and Et3N (0.28 mL, 2.0 mmol). The mixture was allowed to stir for 15 min. and then diluted with diethyl ether. The mixture was then washed with sat'd NaHCO3 (2×) and the organic layer dried with MgSO4. The solvent was then removed in vacuo, the residue redissolved in CH3CN and then treated with Et3N (0.56 mL, 4.0 mmol) and acetone cyanohydrin. The mixture was allowed to stir for 18 h and then diluted with diethyl ether. The mixture was then washed with 1.0N HCl, dried with NaSO4, and the solvent removed in vacuo. Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 3/2 hexane/ethyl acetate) to provide a solid (0.357 g, 66°-68° C.). 1H NMR (400 MHz, CDCl3) δ7.495-7.208 (m, 15H), 3.558 (s, 2H).

Provenance & Evidence