2-Cyclopenten-1-one → HCID 64522109, compound

Participants

Reaction Steps

To 3,4-difluorophenylboronic acid (9.47 g, 60 mmol), cyclopent-2-enone (4.93 g, 60 mmol), antimony trichloride (1.37 g, 6 mmol), sodium acetate, (9.84 g, 120 mmol) and palladium acetate (1.35 g, 6 mmol) are added to acetic acid (300 mL) under an argon atmosphere. The reaction is stirred at room temperature overnight. The reaction mixture is filtered and poured into water. The material is extracted with ethyl acetate (3×), washed with saturated sodium bicarbonate (3×), brine (3×), dried with sodium sulfate, filtered, and concentrated in vacuo. The material is purified using silica gel chromatography eluting with 10% ethyl acetate in pet ether to give the title compound as a yellow oil (6.9 g, 58%). 1H NMR (300 MHz, CDCl3) δ 7.14-6.95 (m, 3H), 3.41-3.37 (m, 1H), 2.64-2.61 (m, 1H), 2.46-2.23 (m, 4H), 1.93-1.84 (m, 1H).

Provenance & Evidence