Ethyl bromoacetate → Ethyl (+/-) 3-(3-methoxyphenyl)indeneacetate

Participants

Reaction Steps

To a cold solution of 3-(3-methoxyphenyl)indene (4 g, 18 mmol), prepared by the method of J. Med. Chem. 1981, 24, 998, in THF (15 mL) at 0° C. was added dropwise a solution of LiN(TMS)2 (20 mL, 1M in THF) over 5 min. The resulting solution was added dropwise to a solution of ethyl bromoacetate (3.34 g, 20 mmol) in THF (15 mL) at −78° C. over 30 min. After 2.5 h, the mixture was quenched with saturated ammonium chloride solution and the layers were separated. The organic layer was dried over MgSO4 and concentrated to give the crude product which was purified by column chromatography (SiO2/2-4% EtOAc/hexane) to give title compound (1.1 g): 1H NMR (400 MHz, CDCl3) δ 1.30 (t, 3H), 2.50 (m, 1H), 2.85 (m, 1H), 3.85 (s, 3H), 4.0 (m, 1H), 4.20 (q, 2H), 6.6 (s, 1H), 6.9 (m, 1H), 7.2 (s, 1H), 7.35 (m, 6H).

Provenance & Evidence