Ethanol → HCID 22117520, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.3 g (1 mmol) of 3-(9-phenyl-9H-fluoren-9-yl)propanal (from Step 2), 0.07 g (1.1 mmol) potassium cyanide and 0.23 g (2.4 mmol) ammonium carbonate in 50% aqueous ethanol (5 mL) was placed in a pressure tube and heated at 60° C. for 16 h with stirring. The reaction was then cooled to room temperature, quenched with 30% acetic acid (5 mL) and most of the solvent removed under vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with water (3×10 mL), dried (MgSO4) and the solvent evaporated. The residue was chromatographed on silica gel with ethyl acetate to provide 0.11 g (yield 30%) of 5-[2-(9-phenyl-9H-fluoren-9-yl)ethyl]hydantoin as a white solid. 1H NMR (CD3OD, 300 MHz) δ: 7.79 (d, 2H), 7.40-7.00 (m, 11H), 3.86 (dd, 1 h), 2.75-2.50 (m, 2H), 1.98 (d, 1H), 1.35-0.8 (m, 3H); 13C NMR (CD3 0D, 75 MHz) δ: 177.8, 159.8, 152.3, 146.0, 142.1, 129.4, 128.9, 128.7, 127.6, 127.5, 125.4 121.1, 59.7, 59.4, 33.6, 27.8.

Provenance & Evidence