Hydrogen Peroxide → 3,5,5-tris(1-ethyl-2-methyl-3-indolyl)-2(5H)-furanone

HRID 544775Notes

Reaction equation

HRID 544775 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[CH:16]=[C:15]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH2:26][CH3:27])[C:18]=3[CH3:28])[O:14][C:13]2=[O:29])=[C:4]1[CH3:30])[CH3:2].[CH2:31]([N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[C:34]1[CH3:42])[CH3:32].OO>C(OC(=O)C)(=O)C>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:13](=[O:29])[O:14][C:15]([C:35]3[C:36]4[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=4)[N:33]([CH2:31][CH3:32])[C:34]=3[CH3:42])([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH2:26][CH3:27])[C:18]=3[CH3:28])[CH:16]=2)=[C:4]1[CH3:30])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1704321H-Indole, 1-ethyl-2-methyl-HCID 204427243,5-Bis(1-ethyl-2-methyl-1H-indol-3-yl)furan-2(3H)-one

Product 1

HCID 204427743,5,5-tris(1-ethyl-2-methyl-3-indolyl)-2(5H)-furanone

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 5.5 g (0.0138 mole) of 3,5-bis(1-ethyl-2-methyl-3-indolyl)-2(3H)-furanone, 8.0 g (0.05 mole) of 1-ethyl-2-methylindole, 100 ml of acetic anhydride and 0.25 ml of 30 percent hydrogen peroxide was stirred approximately eighteen hours at room temperature. The solid was collected by filtration and a small sample showed an infrared maximum at 1800 cm-1 and a smaller maximum at 1745 cm-1. The solid and the filtrate were recombined, and stirred eighteen hours at approximately 60° C. The solid was collected by filtration and dried at 60° C. in vacuo to obtain 3,5,5-tris(1-ethyl-2-methyl-3-indolyl)-2(5H)-furanone (Formula III: R=R2 =CH3CH2 ; R1 =R3 =CH3 ; Y=Y1 =H) as a white solid which melted at 232°-234° C.

Workup

  1. filtrationThe solid was collected by filtration
  2. stirringstirred eighteen hours at approximately 60° C
  3. filtrationThe solid was collected by filtration
  4. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-17aa39a731534ce2bf531bd15f95bf97
Source dataset
uspto-grants-1984_05
Patent number
US04451657

Reaction notes

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