7,8-Bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-chromen-4-one → HCID 59052280, compound

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Reaction Steps

To a solution of 7,8-bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-chromen-4-one (98 mg, 0.254 mmol) in methanol (20 mL) was added Lindlar's catalyst (Pd, 5 wt % on calcium carbonate, 25 mg) under argon. The mixture was stirred at room temperature for 50 min, then it was filtered through a syringe filter and the solvent was evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexanes/10-25%) to give the product as a white solid (72 mg, 73%): 1H NMR (CDCl3, 300 MHz) δ 7.98 (m, 2H), 7.81 (dd, J=0.9, 9.0 Hz, 1H), 7.52 (m, 3H), 7.16 (dd, J=0.6, 9.0 Hz, 1H), 6.75 (d, J=0.6 Hz, 1H), 6.22 (m, 2H), 5.24-5.12 (m, 3H), 4.98 (dd, J=1.2, 10.2 Hz, 1H), 1.56 (s, 6H), 1.55 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 178.1, 163.0, 154.9, 152.5, 136.0, 132.0, 131.2, 128.8, 126.6, 120.5, 119.6, 117.5, 107.3, 85.2, 74.9, 74.1, 73.9, 30.7, 29.8.

Provenance & Evidence