Potassium Carbonate → HCID 59419872, compound

Participants

Reaction Steps

To a suspension of 7-hydroxy-tetralone (0.870 g, 5.3 mmol) and K2CO3 (5 g, excess) in DMF (20 mL) was added ethyl-4-bromobutyrate (0.770 mL, 5.3 mmol) at room temperature and under argon atmosphere. The reaction mixture was stirred at room temperature for ˜16 hours before being poured on ice. The aqueous solution was extracted in ethyl acetate, washed with water, and dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel using ethyl acetate-hexane (2:8) as eluent to give 7-(3-ethoxycarbonylpropoxy)-1-tetralone (1.180 g, 80%): mp 62-63° C., 1H NMR (500 MHz, CDCl3): δ 1.26 (t, J=7.0 Hz, 3H), 2.08-2.14 (m, 4H), 2.48-2.51 (dd, J=7.00 and 7.5 Hz, 2H), 2.62-2.64 (dd, J=6.0 and 6.5 Hz, 2H), 2.88-2.90 (dd, J=6.0 and 6.5 Hz, 2H), 4.02-4.05 (dd, J=6.0 and 6.5 Hz, 2H), 4.15 (q, J=7.0 Hz, 2H), 7.03-7.05 (dd, J=3.0 and 8.0 Hz, 1H), 7.16 (d, J=8.0 Hz, 1H), 7.49 (d, J=3.0 Hz, 1H). HFABMS m/z 277.1436 (calc for C16H20O4, MH+, 277.1440).

Provenance & Evidence