Reaction #40558

Reaction equation

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-benz-imidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

Solvents

toluene

dichloromethane

toluene

Conditions

Workup

1. 1
   workup.STIRRINGstirred at room temperature for 1 hour
2. 2
   Temperaturethe reaction solution is heated
3. 3
   Temperatureto reflux for 3 hours
4. 4
   FiltrationThe reaction solution is filtered through kieselguhr
5. 5
   Washthe residue is washed several times with dichloromethane
6. 6
   Otherthe solvent is removed in a rotary evaporator

Procedure

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.

Source