Ethyl bromoacetate → 2-Ethoxycarbonylmethyl-3-oxo-indan-2,5-dicarboxylic acid-2-ethyl ester-5-methyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-oxo-indan-2,5-dicarboxylic acid 2-ethyl ester-5-methyl ester (Step 1, 500 mg, 1.9 mmol) in dry DMF (0.7 ml) was added sodium hydride (84 mg, 2.0 mmol, 60% in mineral oil) and then heated at 60° C. for 1 h. Then ethyl bromo acetate (350 mg, 2.0 mmol) was dissolved in dry DMF (1.4 ml) and added to the reaction mixture at room temperature and then again heated at 60° C. for 3 h. After completion of the reaction mixture was concentrated and H2O (5 ml) was added. The suspension was extracted with ethyl acetate and combined organic layer was washed with brine, dried and concentrated. The crude was purified by column chromatography using 20% ethyl acetate-hexane to give the desired compound (530 mg). 1H NMR (400 MHz, CDCl3) d 8.42 (1H, s), 8.30 (1H, d), 7.57 (1H, d), 4.37 (4H, m), 3.92 (3H, s), 3.90 (1H, d), 3.28 (2H, m), 2.90 (1H, d), 1.15 (3H, m) ppm.

Provenance & Evidence