HCID 50900629, compound → HCID 50900630, compound

Participants

Reaction Steps

Compound 2 (0.121 g, 0.46 mmol) was stirred at room temperature in MeOH (4.6 mL). To this, CuCl (0.137 g, 1.38 mmol) was added and mixture stirred at room temperature for 5-10 min. KBH4 (0.174 g, 3.22 mmol) was added in portions. The reaction was stirred at room temperature until the solution became clear. The reaction was quenched with deionized H2O and extracted 3 times with 15 mL of a 90:10 mixture of ethyl acetate:dichloromethane. The organic layers were combined and dried over Na2SO4. The solvent was removed to give a brownish-black solid (107 mg, 100% yield). 1H NMR (300 MHz, CDCl3) δ 7.32 (1H, dd, J=7.8, 1.4 Hz), 7.25 (1H, dd, J=7.3, 1.7 Hz), 7.22 (1H, dd, J=7.1, 1.7 Hz), 7.16, (1H, dd, J=8.0, 1.6 Hz), 7.00-6.95 (2H, m), 6.76 (1H, ddd, J=9.3, 7.7, 1.4 Hz), 6.67 (1H, ddd, J=8.9, 7.6, 1.5 Hz); 13C (75 MHz, CDCl3) δ 147.6 (q), 142.2 (q), 136.9 (q), 130.7 (t), 130.68 (q), 127.4 (t), 125.5 (t), 123.6 (t), 121.9 (t), 118.6 (t), 115.8 (t), 41.1.

Provenance & Evidence