Ammonium Hydroxide → 4-(Thiophen-3-yl)butanoic acid

HRID 1526741Notes

Reaction equation

HRID 1526741 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH:8](C(O)=O)[C:9]([OH:11])=[O:10])=[CH:2]1.[OH-].[NH4+]>COCCOCCOC>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:2]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 54550536[2-(Thiophen-3-yl)ethyl]propanedioic acid

Product 1

HCID 110411434-(Thiophen-3-yl)butanoic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

The product from Step C (2.4 g, 11.0 mmol) was dissolved in 2-methoxyethyl ether (20 mL) and refluxed for 24 hours. The reaction was cooled to room temperature and basified to pH 9 with concentrated ammonium hydroxide. The mixture was extracted once with diethyl ether and set aside. The aqueous layer was acidified with concentrated hydrochloride acid and extracted four times with diethyl ether. The extract were combined and dried over sodium sulfate, filtered and concentrated to give 4-thiophen-3-yl-butyric acid (1.8 g, 95%) as an oil.

Workup

  1. temperaturerefluxed for 24 hours
  2. extractionThe mixture was extracted once with diethyl ether
  3. extractionextracted four times with diethyl ether
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82b71211a51140d3b9dee9e3a0c52522
Source dataset
uspto-grants-2015_07
Patent number
US09085531B2

Reaction notes

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