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

HRID 485337Notes

Reaction equation

HRID 485337 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.S(Cl)(Cl)=O.[CH2:19](O)[CH3:20]>>[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]([O:14][CH2:19][CH3:20])=[O:13])=[CH:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 37441H-Indole-3-propanoic acidHCID 24386Thionyl Chloride

Product 1

HCID 225390Ethyl 3-(1h-indol-3-yl)propanoate

Procedure

A solution of 7.38 g of 3-indolepropionic acid and 5.9 g of thionyl chloride in 50 ml of ethanol is refluxed for 2 hours, cooled and evaporated. The residue is partitioned between ether and cold sodium bicarbonate solution. The organic phase is separated, dried over sodium sulfate and evaporated to yield ethyl 3-(3-indolyl)propionate; Rf (ether/SiO2)=0.51; IR (CH2Cl2) 1725 cm-1.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue is partitioned between ether and cold sodium bicarbonate solution
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-5994383167854f419bf372b83aea7c1e
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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