Ethanol → Ethyl 3-(1h-indol-3-yl)propanoate

HRID 422833Notes

Reaction equation

HRID 422833 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1.[CH2:15](O)[CH3:16]>S(=O)(=O)(O)O>[CH2:15]([O:13][C:12](=[O:14])[CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH3:16]

Participants

4

Reactant 2

HCID 702EthanolHCID 37441H-Indole-3-propanoic acid

Product 1

HCID 225390Ethyl 3-(1h-indol-3-yl)propanoateYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of 3-indolepropionic acid (4.00 g, 1 eq) in ethanol (70 ml), 1 ml of sulphuric acid is added dropwise and the mixture is first refluxed overnight and then evaporated to dryness. The resulting crude residue is dissolved in ethyl acetate and the organic solution is washed with 5% aqueous sodium bicarbonate, water, dried over MgSO4, filtered and finally evaporated to dryness, to afford the title compound as a yellow solid (4.30 g, 95% yield), which is used as such for the next step.

Workup

  1. additionis added dropwise
  2. temperaturethe mixture is first refluxed overnight
  3. customevaporated to dryness
  4. dissolutionThe resulting crude residue is dissolved in ethyl acetate
  5. washthe organic solution is washed with 5% aqueous sodium bicarbonate, water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customfinally evaporated to dryness

Sources & evidence

ORD record
ord-10b21e762fdd4471a127c7e5e600d390
Source dataset
uspto-grants-2012_01
Patent number
US08101649B2

Reaction notes

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