Potassium Hydroxide → HCID 20080316, compound

HRID 1653619Notes

Reaction equation

HRID 1653619 reaction equation
[CH3:1][C:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.[OH-].[K+]>C(Cl)(Cl)Cl>[CH3:11][C:10]1([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[C:2]1=[CH2:1]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 154273H-Indole, 2,3,3-trimethyl-HCID 1650214-Methoxybenzyl bromide

Product 1

HCID 20080316HCID 20080316, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4.0 g of 2,3,3-trimethylindolenine in 25 ml of chloroform was added 5.6 g of p-methoxybenzyl bromide and the mixture was heated in an autoclave at 80° C. for 21 hours. The resulting precipitate was recovered by filtration to give 8.5 g of 1-(4-methoxybenzyl)-2,3,3-trimethylindolenium as white crystals. To these crystals was added 85 ml of 10N aqueous potassium hydroxide solution in a nitrogen atmosphere and the mixture was heated at 50° C. for 3 hours. The reaction mixture was then extracted with ether and the extract was dried over magnesium sulfate and concentrated under reduced pressure to give 5.7 g of 3,3-dimethyl-1-(4-methoxybenzyl)-2-methyleneindoline (Yield 80.6%).

Workup

  1. filtrationThe resulting precipitate was recovered by filtration
  2. customto give 8.5 g of 1-(4-methoxybenzyl)-2,3,3-trimethylindolenium as white crystals
  3. temperaturethe mixture was heated at 50° C. for 3 hours
  4. extractionThe reaction mixture was then extracted with ether
  5. dry with materialthe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f8a6741dc234e5f920f184ff5e5754f
Source dataset
uspto-grants-1995_04
Patent number
US05403702

Reaction notes

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