Triacetoxyperiodinane → 1-(4,6-Dichloro-5-pyrimidinyl)ethanone

Participants

Reaction Conditions

Reaction Steps

1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane; 1.3 g, 3.1 mmol) was added to a solution of 1-(4,6-dichloro-pyrimidin-5-yl)-ethanol (from Step 1; 540 mg, 2.8 mmol) in dichloromethane at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 5 min and then at room temperature for 90 min. Saturated aqueous sodium bicarbonate solution was added and the mixture was extracted with dichloromethane (3×50 mL). The organic layers were washed with water and brine, dried (sodium sulfate), filtered, and evaporated. The residue was triturated twice with ether/petroleum ether (2:1), the solvent was decanted and the solvent was evaporated to give 1-(4,6-dichloro-pyrimidin-5-yl)-ethanone (500 mg, 93%) which was used directly in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 2.64 (s, 3H), 8.83 (s, 1H).

Provenance & Evidence