1-p-Tolyl-hex-5-en-1-yn-3-ol → 1-p-Tolyl-bicyclo[3.1.0]hexan-3-one

Participants

Reaction Conditions

Reaction Steps

PtCl2 (157 mg; 5 mol %) was added to a solution of 1-p-tolyl-hex-5-en-1-yn-3-ol (2.20 g; 11.8 mmol) in toluene (60 mL) and the resulting mixture was stirred at 80° C. for 24 h until the reaction was complete as shown by TLC. The toluene was concentrated at 45-50° C. using a rotary evaporator, and the residue was purified by flash chromatography (9:1→3:1 heptane/EtOAc) to give the desired product (880 mg; 40%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.68 (t, 1 H) 1.26-1.30 (m, 1 H) 1.92-1.97 (m, 1 H) 2.33 (s, 3 H) 2.39 (d, 1 H) 2.60-2.65 (d, 1H) 2.75-2.86 (m, 1 H) 2.88-2.93 (m, 1H) 7.07-7.14 (m, 4H).

Provenance & Evidence