Ethyl Acetate → Butyl 1-oxoindane-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-1-indanone (5.0 g, 23.7 mmol), DIEA (14.4 mL, 82.9 mmol) and PdCl2(PPh3)2 in n-BuOH (50 mL) was purged with carbon monoxide for 5 min and then stirred under a CO balloon at 115° C. for 2 h. The reaction mixture was allowed to cool to room temperature and filtered through Celite. Solvent evaporation in vacuo followed by filtration on a short column of silica gel and eluted with CH2Cl2 gave the crude product. Chromatography (10% EtOAc in Hexane) afforded butyl 1-oxoindane-5-carboxylate. HPLC/MS: m/z=233.1 (M+1), Rt=3.55 min. 1H NMR (CDCl3): δ 8.18 (1H, s), 8.06 (1H, d, J=8.0 Hz), 7.82 (1H, d, J=8.0 Hz), 4.39 (2H, t, J=6.5 Hz), 3.23 (2H, t, J=6.0 Hz), 2.78 (2H, t, J=6.0 Hz), 1.81 (1H, m), 1.52 (2H, m), 1.02 (3H, t, J=7.0 Hz).

Provenance & Evidence