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

HRID 1983911Notes

Reaction equation

HRID 1983911 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-9c90216954bf4927a8235bd0c0a38fe0
Source dataset
uspto-grants-2009_06
Patent number
US07541357B2

Reaction notes

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