Potassium Carbonate → HCID 67128562, compound

Participants

Reaction Steps

Compound 1 (0.3 g, 1.3 mmol) was dissolved in 10 mL CH3CN and 1,6-dibromohexane (4.85 g, 19 mmol), and potassium carbonate (0.37 g, 2.6 mmol) was added. The reaction mixture stirred overnight at room temperature. The solvent was evaporated to a minimum volume and purified by silica gel chromatography eluting with 100% CH2Cl2 twice and several times with 0.5% methanolic NH3 (7 M NH3 in methanol)/99.5% CH. The organic layers were combined and rotovaped (61.5%). 1H NMR (CDCl3) δ 8.480 (d, 1H, Ar), 7.612 (t, 1H, Ar), 7.553 (d, 1H, Ar), 7.474 (d, 1H, Ar), 7.192 (t, 1H, Ar), 7.097 (t, 1H, Ar), 6.923 (t, 1H, Ar), 6.824 (d, 1H, Ar), 3.776 (overlapped s, 5H, —CH2—, —OCH3), 3.671 (s, 2H, —CH2—), 3.328 (m, 2H, —CH2—), 2.488 (ddd, 2H, —CH2—), 1.783 (p, 2H, —CH2—), 1.531 (m, 2H, —CH2—), 1.331 (p, 2H, —CH2—), 1.271 (p, 2H, —CH2—). Mass Spect=391.14 (M+H)+.

Provenance & Evidence