Iodoethane → HCID 10198161, compound

HRID 2120252Notes

Reaction equation

HRID 2120252 reaction equation
[CH2:1](I)[CH3:2].[OH:4][CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][C:10](=[O:16])[NH:11]2>ClCCl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][C:10](=[O:16])[NH:11]2)[CH3:2]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 10198161HCID 10198161, compoundYield 29.2%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Ethyl iodide (o.47 mL, 6 mmol) was added to a stirred mixture of silver trifluoromethanesulfonate (1.35 g, 5.2 mmol) 2,6-di-tert-butylpyridine (1 g, 5.2 mmol) and 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (0.53 g, 3 mmol) in dichloromethane (10 mL) at 0° C. The mixture was warmed to room temperature and stirred for 2 hours. The precipitate formed after 5-10 minutes changed color from yellow to brown. The reaction mixture was diluted with dichloromethane (100 mL) and washed with 1 N hydrochloric acid, saturated sodium bicarbonate and brine, dried and concentrated. The residue was chromatographed on silica gel to give 180 mg (29%) of 4-(2-ethoxy-ethyl)-1,3-dihydro-indol-2-one as a purple oil.

Workup

  1. customThe precipitate formed after 5-10 minutes
  2. washwashed with 1 N hydrochloric acid, saturated sodium bicarbonate and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-8af329a11c46417eae3a960ce3468923
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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