Trifluoroacetic acid → HCID 66914731, compound

HRID 880464Notes

Reaction equation

HRID 880464 reaction equation
FC(F)(F)C(O)=O.[CH:8]([C:11]1[CH:15]=[CH:14][N:13]([CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[CH:12]=1)([CH3:10])[CH3:9]>ClCCl>[CH:8]([C:11]1[CH:15]=[CH:14][N:13]([CH2:16][C:17]([OH:19])=[O:18])[CH:12]=1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66914838HCID 66914838, compound

Product 1

HCID 66914731HCID 66914731, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.20 mL, 15.70 mmol) was added to a solution of tert-butyl 2-(3-isopropyl-pyrrol-1-yl)acetate (350 mg, 1.57 mmol) in dichloromethane at 0° C. and the reaction mixture was stirred at ambient temperature for 16 h. The solvent was evaporated in vacuo and the residue was basified with saturated sodium bicarbonate solution. The solution was washed with diethyl ether and the alkaline solution was then acidified with concentrated aqueous HCl and extracted with diethyl ether. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give 2-(3-isopropylpyrrol-1-yl)acetic acid (180 mg, 69%) as a semi-solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. washThe solution was washed with diethyl ether
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0739211d40e8476d82b6fe4487f71859
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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