Water → HCID 64521714, compound

Participants

Reaction Conditions

Reaction Steps

A 40 mL vial was charged with (3-fluorophenyl)boronic acid (1.278 g, 9.14 mmol) and purged with nitrogen for 10 min. The reaction vessel was then sequentially charged with dioxane (15.2 mL), an aqueous solution of sodium carbonate (5.1 mL, 1.9 M), and 2-cyclopenten-1-one (0.510 ml, 6.09 mmol) via syringe. Chloro(1,5-cyclooctadiene)rhodium (I) dimer (0.090 g, 0.183 mmol) was introduced in a single portion. The vial was sealed with a PTFE line cap and the resultant reaction mixture was heated to 90° C. After 2 h, the reaction mixture was allowed to cool to RT and poured into a mixture of water (30 mL) and EtOAc (30 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (50-g Biotage column, eluent: gradient, 0 to 100% EtOAc in heptane with 10% CH2Cl2 as an additive) to afford 3-(3-fluorophenyl)cyclopentanone (668 mg, 3.75 mmol, 61.6% yield) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.37-7.23 (m, 1H), 7.08-6.99 (m, 1H), 6.99-6.89 (m, 1H), 3.50-3.33 (m, 1H), 2.68 (dd, J=7.7, 18.3 Hz, 1H), 2.53-2.40 (m, 2H), 2.39-2.25 (m, 2H), 2.05-1.90 (m, 1H). m/z (ESI) 179.2 (+H)+.

Provenance & Evidence