p-Toluenesulfonic acid → 1-(3-Nitro-pyrazol-1-ylmethyl)-cyclopropanol

Participants

Reaction Conditions

Reaction Steps

The 3-nitro-1-[1-(tetrahydro-pyran-2-yloxy)-cyclopropylmethyl]-1H-pyrazole (326 mg, 1.22 mmol) was dissolved in ethanol (7 mL) and p-toluene sulfonic acid (50 mg, 0.29 mmol) was added. After stirring at 25° C. for 1.5 h, the solution was concentrated in vacuo to give an oil. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 50% ethyl acetate/hexanes) afforded 1-(3-nitro-pyrazol-1-ylmethyl)-cyclopropanol (158 mg, 71%) as an oil: H1-NMR (400 MHz, CDCl3) δ 0.81-0.86 (2H, m), 0.97-1.02 (2H, m), 2.78 (1H, bs), 4.31 (2H, s), 6.92 (1H, d, J=2.4 Hz), 7.61 (1H, d, J=2.4 Hz).

Provenance & Evidence