Triacetoxyperiodinane → 1-Benzyl-1H-pyrazole-4-carbaldehyde

Participants

Reaction Steps

(1-Benzyl-1H-pyrazol-4-yl)methanol (190 mg, 1.0 mmol) in DCM (8 mL) at rt was treated with Dess-Martin periodinane (670 mg, 1.58 mmol). After 1.5 h, the reaction was quenched with a mixture of saturated solution of sodium thiosulfate and 10% NaHCO3 (1:1) at rt, stirred for 30 min before extraction with DCM (3×30 mL). The combined extracts were washed with a saturated aqueous solution of NaHCO3, brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (Isco CombiFlash) 0-40% EtOAc/heptane provided 1-benzyl-1H-pyrazole-4-carbaldehyde (86 mg, 46%). 1H NMR (400 MHz, CDCl3) δ ppm 5.35 (s, 2H), 7.27-7.30 (m, 2H), 7.36-7.43 (m, 3H), 7.88 (s, 1H), 8.01 (s, 1H), 9.85 (s, 1H); LCMS-MS (ESI+) 186.90 (M+H).

Provenance & Evidence