Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | 4-Methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone | HCID 68491977 | — |
| Solvent | Nitromethane | HCID 6375 | — |
| Product | HCID 68490938 | HCID 68490938 | 84.2% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07745641B2 |
|---|
| Source dataset | uspto-grants-2010_06 |
|---|
| ORD ID | ord-1cb350f87c7445c2a2e5b2399842f494 |
|---|
| Source note | uspto-grants-2010_06 |
|---|