6-Chloro-4-(6-methoxycarbonyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one → 6-Chloro-4-(6-formyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

Participants

Reaction Conditions

Reaction Steps

6-Chloro-4-(6-methoxycarbonyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one (3.0 g, 5.3 mmol) is dissolved in dichloromethane, and the solution is cooled to 0° C. 15% DIBA1H in toluene is added dropwise, and the reaction mixture is stirred at room temperature for 1 hour. A further 15% DIBA1H in toluene is then added dropwise at 0° C. and stirred at room temperature for 1 hour. Manganese(IV) oxide is then added directly and the reaction solution is heated to reflux for 3 hours. Additional manganese oxide is added every 3 hours until the conversion is complete according to LC-MS. The reaction solution is filtered through kieselguhr, the residue is washed several times with dichloromethane, and the solvent is removed in a rotary evaporator.

Provenance & Evidence