Stannous Chloride → HCID 69507304, compound

Participants

Reaction Steps

To a solution of biphenyl vi (800 mg, 1.85 mmol) in EtOH (20 mL) was added tin(II) chloride (1.76 g, 9.26 mmol). The mixture was heated at reflux for 16 h and then cooled to room temperature. The reaction mixture was diluted with EtOAc (50 mL) and basified with saturated aqueous NaHCO3. The resulting white suspension was stirred at room temperature for 30 min, then filtered through celite and the precipitate was washed by EtOAc (3×20 mL). The two layers were separated and the organic layer was collected. The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine and dried over MgSO4. After the solvent was removed under reduced pressure, the residue was purified by flash chromatography (EtOAc/hexane, 40% to 70%) to yield vii as a light yellow solid (500 mg, 73%). 1H NMR (CDCl3): δ 7.93 (br s, 1H), 7.14 (t, J=8.4 Hz, 1H), 6.73 (m, 2H), 6.51 (d, J=8.4 Hz, 1H), 3.62 (s, 6H), 3.37 (s, 3H), 1.34 (s, 6H). Anal. Calcd for C20H22N2O5: C, 64.85; H, 5.99; N, 7.56. Found: C, 65.00; H, 5.73; N, 7.31.

Provenance & Evidence