Tempo → 4-Prop-2-ynylcyclohexanecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of Compound 9 (2.45 g, 16 mmol) in 50% acetonitrile/water (35 mL) cooled to 0° C. was added bis-acetoxy-iodobenzene (BAIB) (11.4 g, 35 mmol) and TEMPO (502 mg, 3.2 mmol). The reaction mixture was stirred at 0° C. for 1 hour, then for 90 minutes at room temperature. The solvents were evaporated, and the residue dissolved in 1/1 CH3CN/H2O (100 mL). Once again the solvents were evaporated, and this procedure repeated to remove iodobenzene as its azeotrope. The resulting Compound 11 (2.53 g, 95%) was obtained as a brown sticky solid that was not further purified but carried forward into the next step. 1H-NMR (600 MHz, CD3OD): 1.13 (dq, 2H), 1.45 (dq, 2H), 1.48 (m, 1H), 1.93 (dd, 2H), 2.03 (dd, 2H), 2.12 (dd, 2H), 2.2-2.3 (m, 2H).

Provenance & Evidence