Reaction #49364

Reaction equation

water

trifluoroacetic acid

triethylsilane

4-methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

→

4-methoxymethoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

Yield 84.2%

Solvents

nitromethane

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   OtherThe solvent was evaporated under reduced pressure
5. 5
   OtherThe residue was purified by flash column chromatography (chloroform/methanol=100/0, 99/1, hexane/ethyl acetate=80/20, 60/40)

Procedure

In a similar manner to Step 4 of Example 16, 4-methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (1.15 g, 2.54 mmol) was dissolved in nitromethane (58 mL), and the solution was added with trifluoroacetic acid (1.20 mL, 7.62 mmol) and triethylsilane (0.587 mL, 7.62 mmol), followed by stirring at room temperature for 30 minutes. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (chloroform/methanol=100/0, 99/1, hexane/ethyl acetate=80/20, 60/40) to obtain 4-methoxymethoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (935 mg, yield 84%).

Source