Iodoethane → HCID 54370545, compound

Participants

Reaction Steps

To 5 ml of a DMF solution containing 200 mg (0.5181 mmol) of 2,2'-dihydroxy-5,5'-bis (2-ethoxycarbonylethyl) biphenyl and 0.423 ml (5.181 mmol) of ethyl iodide, there were added 85.8 mg (0.6217 mmol) of anhydrous potassium carbonate and a small amount of copper powder and the resulting mixture was agitated overnight at room temperature. The reaction mixture was filtered by suction through Celite to remove the solid matte rand the filtrate was washed with ethyl acetate. After the solvent in the filtrate was evaporated off under reduced pressure, the evaporated residue was dissolved in chloroform. This solution was washed with dilute hydrochloric acid, dilute aqueous sodium bicarbonate, water and aqueous sodium chloride solution in this sequence and was dried by adding anhydrous sodium sulfate. The residue obtained after the solvent had been evaporated off was purified by silica gel column chromatography (with 20 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 100/1 and 75/1) to obtain 141.6 mg (0.3420 mmol, 66%) of 2-ethoxy-2'-hydroxy-5,5'-bis (2-ethoxycarbonylethyl) biphenyl as an oily product. 1H-NMR (CDCl3) δ (ppm): 1.24 (6H, t, 2CH3), 1.36 (3H, t, CH3), 2.62 (2H, t, CH2), 2.63 (2H, t, CH2), 2.94 (2H, t, CH2), 2.95 (2H, t, CH2), 4.11 (`6H, q, CH2), 4.13 (4H, q, 2CH2), 6.66 (1H, s, OH), 6.9-7.3 (6H, m, arom-H) MS (FAB): 414 (M+)

Provenance & Evidence