Methyl iodide → HCID 10313470, compound

HRID 2120251Notes

Reaction equation

HRID 2120251 reaction equation
[CH3:1]I.[OH:3][CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][C:9](=[O:15])[NH:10]2>ClCCl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:1][O:3][CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][C:9](=[O:15])[NH:10]2

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 10313470HCID 10313470, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Methyl iodide (1.41 g, 10 mmol) was added to a stirred mixture of silver trifluoromethanesulfonate (2.56 g, 10 mmol) and 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (0.88 g, 5 mmol) in dichloromethane (20 mL) at 0° C. The precipitate formed after 5-10 minutes changed color from yellow to gray then dark purple. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane and filtered through celite. The filtrate was concentrated and chromatographed on silica gel to give 4-(2-methoxy-ethyl)-1,3-dihydro-indol-2-one.

Workup

  1. customThe precipitate formed after 5-10 minutes
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-504974ef0ffe4b689b5e0c0ca38fc983
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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