Sodium Bicarbonate → HCID 39733625, compound

Participants

Reaction Steps

To a solution of commercially available 4-hydroindole (compound 1, 0.226 g, 1.7 mmol) and potassium carbonate (0.704 g, 5.1 mmol) in acetone was added ethyl bromoacetate (0.3 mL, 2.6 mmol). The reaction mixture was stirred at RT for 18 h, and then filtered. The solvent was removed and the green oil was purified by flash chromatography [hexanes-ethyl acetate (4:1)] to give ethyl(indol-4-yloxy)acetate. NMR: δ (300 MHz, CDCl3) 8.2 (br s, 1H), 7.13 (dd, J=5.6, 2.3 Hz, 1H), 7.1-7.06 (m, 2H), 6.73 (t, J=2.4 Hz), 6.43 (dd, J=5.9, 2.7 Hz, 1H), 4.78 (s, 2H), 4.28 (q, J=7.4 Hz, 2H), 1.31 (t, J=7.4 Hz, 3H). To a solution of this indole in acetic acid (10 mL) was added sodium cyanoborohydride (0.302 g, 4.8 mmol) as a solid. The reaction mixture was stirred at RT for 18 h, then neutralized with aqueous sodium bicarbonate and extracted with diethyl ether. The solvent was removed to give compound 2a (0.308 g, 88% yield) as a colorless oil. NMR: δ (300 MHz, CDCl3) 6.98 (d, J=7.9 Hz, 1H), 6.39 (t, J=7.9 Hz, 1H), 6.18 (d, J=7.9 Hz, 1H), 4.62 (s, 2H), 4.28 (q, J=7.0, Hz, 2H), 3.58 (t, J=8.4 Hz, 2H), 3.07 (t, J=8.4 Hz, 2H), 1.30 (t, J=7.0 Hz, 3H).

Provenance & Evidence