HCID 178507804, compound → HCID 135486169, compound

Participants

Reaction Steps

The alkyne (5-4, 56 mg, 0.161 mmol) was dissolved in acetic acid (8 mL) and treated with mercuric acetate (77 mg, 0.24 mmol). After 2 h stirring, the reaction mixture was concentrated in vacuo, suspended in saturated aqueous sodium bicarbonate and treated with sodium borohydride. After 10 min stirring, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. Chromatography (SiO2, 50% ethyl acetate in hexanes) afforded the desired product (5-5); 1H NMR (300 MHz, DMSO-d6) δ 13.58 (s, 1H), 12.09 (s, 1H), 8.26 (d, 1H, J=8.7 Hz), 8.11 (s, 1H), 7.72 (d, 1H, J=1.5 Hz), 7.61 (dd, 1H, J=8.7, 1.8 Hz), 7.55 (d, 1H, J=8.4 Hz), 7.36 (d, 1H, J=1.5 Hz), 7.30 (dd, 1H, J=8.7, 1.8 Hz), 7.16 (s, 2H).

Provenance & Evidence