Reaction #49542

Reaction equation

4-Methanesulfonyloxy-5-formyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

trimethyl orthoformate

sodium hydrogencarbonate

water

→

4-methanesulfonyloxy-5-dimethoxymethyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

Yield 96.5%

Solvents

methanol

Conditions

Workup

1. 1
   FiltrationThe precipitated solid was collected by filtration
2. 2
   Washwashed with water
3. 3
   Otherby drying under reduced pressure

Procedure

4-Methanesulfonyloxy-5-formyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (220 mg, 0.416 mmol) was dissolved in methanol (4 mL), and the solution was added with trimethyl orthoformate (0.091 mL, 0.83 mmol) and p-toluenesulfonic acid monohydrate (1.0 mg, 0.0058 mmol), followed by stirring at 50° C. for 5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and water. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 4-methanesulfonyloxy-5-dimethoxymethyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (231 mg, yield 96%).

Source