Ethanol → HCID 54423884, compound

Participants

Reaction Steps

To ethanol (2.0 ml) was added sodium metal (15 mg) at room temperature. After 25 minutes, 3-bromomethyl-4-[3-(tert-butoxycarbonyl-tert-butyl-amino)-propoxy]-benzofuran-2-carboxylic acid ethyl ester (98 mg) was added to the reaction mixture. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (10 ml) and water (20 ml). The product was extracted with ethyl acetate (10 ml) 3 times. Organic layer was combined and dried over anhydrous sodium sulfate, concentrated in vacuo to dryness. The residue was purified by silica gel column chromatography developed by hexane-ethyl acetate to give 4-[3-(tert-butoxycarbonyl-tert-butyl-amino)-propoxy]-3-ethoxymethyl-benzofuran-2-carboxylic acid ethyl ester (70 mg) as a pale yellow oil. FAB-MS: m/z 478 (MH+); 1H-NMR (CDCl3): δ 1.22 (3H, t, J=6.9 Hz), 1.37-1.47 (21H, m), 2.09 (2H, quintet, J=7.3 Hz), 3.54 (2H, t, J=7.3 Hz), 3.62 (2H, q, J=6.9 Hz), 4.12 (2H, t, J=7.3 Hz), 4.45 (2H, q, J=7.3 Hz), 5.06 (2H, s), 6.65 (1H, d, J=7.9 Hz), 7.14 (1H, d, J=7.9 Hz), 7.33 (1H, dd, J=7.9 Hz, 7.9 Hz).

Provenance & Evidence