Hydroquinone → 1-(2-Methacryloyloxyethyl)indole

HRID 2228369Notes

Reaction equation

HRID 2228369 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[C:13]([O-:18])(=[O:17])[C:14]([CH3:16])=[CH2:15].[K+].[I-].[K+].C1(C=CC(O)=CC=1)O>CN(C)C=O>[C:13]([O:18][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)(=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 4875Potassium IodideHCID 108992601-(2-chloroethyl)-1H-indoleHCID 23667354Potassium methacrylate

Product 1

HCID 184697791-(2-Methacryloyloxyethyl)indoleYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Next, to a flask of 200 ml capacity fitted with a stirrer and cooling tube, there were introduced 15.4 g of 1-(2-chloroethyl)indole, 21.3 g of potassium methacrylate, 7.1 g of potassium iodide, 40 ml of N,N-dimethyl formamide and a small amount of hydroquinone. The mixture was heated to 100° C. and was stirred for 2.5 hours. After completion of the reaction, the insoluble material was removed by filtration, and concentration was performed under reduced pressure. This reaction mixture was then purified by column chromatography using silica gel, to obtain 15.5 g of 1-(2-methacryloyloxyethyl)indole.

Workup

  1. customNext, to a flask of 200 ml capacity fitted with a stirrer
  2. temperaturecooling tube
  3. customAfter completion of the reaction
  4. customthe insoluble material was removed by filtration, and concentration
  5. customThis reaction mixture was then purified by column chromatography

Sources & evidence

ORD record
ord-635e3ff93a264caeb7583e02896f6427
Source dataset
uspto-grants-2002_07
Patent number
US06416939B1

Reaction notes

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