Hydroquinone → 1-(2-Methacryloyloxyethyl)indole

HRID 1108540Notes

Reaction equation

HRID 1108540 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

Subsequently, 1-(2-chloroethyl)indole (15.4 g), potassium methacrylate (21.3 g), potassium iodide (7.1 g), N,N-dimethylformamide (40 ml), and a small amount of hydroquinone were placed in a 200-ml flask equipped with a stirrer and a condenser tube. The mixture was heated to 100° C. and stirred for 2.5 hours. After completion of reaction, insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. This reaction mixture was purified further by silica gel column chromatography to obtain 1-(2-methacryloyloxyethyl) indole (15.5 g).

Workup

  1. customequipped with a stirrer and a condenser tube
  2. customAfter completion of reaction, insoluble matter
  3. customwas removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThis reaction mixture was purified further by silica gel column chromatography

Sources & evidence

ORD record
ord-cbd6d095bfb2494e95f2835fc96b22b3
Source dataset
uspto-grants-2000_05
Patent number
US06068963

Reaction notes

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