HCID 11788723, compound → 3-(4-Methoxyphenyl)cyclopentan-1-one

Participants

Reaction Steps

To a RT solution of 3-(4-methoxyphenyl)cyclopent-2-en-1-one (Step A) (4.68 g, 24.86 mmol) in EtOAc (100 ml) was added Pd/C (Degussa E101 NE/W, 10% dry weight, 50% water) (2.65 g, 1.243 mmol). The reaction mixture was degassed and flushed with nitrogen, then, degassed and flushed with hydrogen using a balloon. After 2 hours filtered reaction through a pad of Celite® washing with EtOAc. The filtrate was and purified by flash column chromatography on silica gel, eluting EtOAc in hexanes to afford the title compound as a racemic mixture. 1H NMR (500 MHz, CDCl3): δ 7.18 (d, J=8.5 Hz, 1H); 6.88 (d, J=8.6 Hz, 1H); 3.80 (s, 3H); 3.42-3.32 (m, 1H); 2.65 (dd, J=18.1, 7.4 Hz, 1H); 2.48-2.36 (m, 2H); 2.34-2.23 (m, 2H); 2.00-1.90 (m, 1H).

Provenance & Evidence