1-(3,4-Dichlorophenyl)hex-5-en-1-yn-3-ol → 1-(3,4-Dichlorophenyl)bicyclo[3.1.0]hexan-3-one

Participants

Reaction Conditions

Reaction Steps

PtCl2 (5 mol %) was added to a solution of 1-(3,4-dichlorophenyl)hex-5-en-1-yn-3-ol (2.98 g; 12.36 mmol) in toluene (65 mL) and the resulting mixture was stirred at 80° C. for 30 h until the reaction was complete by TLC. The toluene was concentrated at 45-50° C. using a rotary evaporator, and the residue was purified by flash chromatography (9:1→2:1 heptane/EtOAc) to give the desired product (895 mg; 30%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.68 (t, 1 H) 1.25-1.30 (m, 1 H) 1.90-1.99 (m, 1 H) 2.36-2.41 (d, 1 H) 2.59-2.64 (d, 1 H) 2.80-2.89 (m, 2 H) 7.00 (d, 1H) 7.25 (s, 1H) 7.37 (d, 1 H).

Provenance & Evidence