2,4-Bis(1-ethyl-2-methyl-3-indolyl)-4-oxobutanoic acid → 3,5-Bis(1-ethyl-2-methyl-1H-indol-3-yl)furan-2(3H)-one

HRID 616784Notes

Reaction equation

HRID 616784 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]([CH2:16][C:17]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][CH3:29])[C:20]=2[CH3:30])=O)[C:13]([OH:15])=[O:14])=[C:4]1[CH3:31])[CH3:2]>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]([CH:12]2[CH:16]=[C:17]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH2:28][CH3:29])[C:20]=3[CH3:30])[O:15][C:13]2=[O:14])=[C:4]1[CH3:31])[CH3:2]

Participants

3

Reactant 1

HCID 204427762,4-Bis(1-ethyl-2-methyl-3-indolyl)-4-oxobutanoic acid

Product 1

HCID 204427243,5-Bis(1-ethyl-2-methyl-1H-indol-3-yl)furan-2(3H)-oneYield 88.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 40.0 g (0.096 mole) of 2,4-bis(1-ethyl-2-methyl-3-indolyl)-4-oxobutanoic acid (prepared as in Example 3, part A) and 450 ml of acetic anhydride was stirred approximately seventeen hours at ambient temperature under an atmosphere of air. The solid that formed was collected by filtration and washed first with acetic anhydride and then with diethyl ether. After drying at 60° C in vacuo there was obtained 34.0 g of 3,5-bis(1-ethyl-2-methyl-3-indolyl)-2(3H)-furanone (Formula II: R=CH3CH2 ; R1 =CH3 ; Y=H) as a white solid which melted over the range 186°-188° C with decomposition.

Workup

  1. customThe solid that formed
  2. filtrationwas collected by filtration
  3. washwashed first with acetic anhydride
  4. customAfter drying at 60° C in vacuo

Sources & evidence

ORD record
ord-2814713950c844259683e8bee1eaa1da
Source dataset
uspto-grants-1978_02
Patent number
US04075224

Reaction notes

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