Sodium Carbonate → HCID 89580481, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (500 mg, 2.6 mmol), tert-butyl 4-bromobenzoate (512 mg, 2 mmol), sodium carbonate (636 mg, 6 mmol) and tetra(triphenylphosphine) palladium (115 mg, 0.1 mmol) in 1,4-dioxane (20 mL) and water (4 mL) was stirred for 15 hours at 90° C. under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1) to give tert-butyl 4-cyclopentenylbenzoate (400 mg, 82%) as a yellow oil. LRMS (M+H+) m/z: calcd 244.15. found 244. 1H NMR (300 MHz, CD3OD): δ 7.94-7.91 (m, 2H), 7.58-7.54 (m, 2H), 6.43-6.42 (m, 1H), 2.78-2.76 (m, 2H), 2.61-2.59 (m, 2H), 2.11-2.08 (m, 2H), 1.64 (s, 9H).

Provenance & Evidence