ChemicalBook CAS DataBase List (PYRROL-3-YL)-ACETIC ACID

(PYRROL-3-YL)-ACETIC ACID synthesis

6synthesis methods

Product Name:(PYRROL-3-YL)-ACETIC ACID
CAS Number:86688-96-2
Molecular formula:C6H7NO2
Molecular Weight:125.13

138779-98-3 Synthesis

1H-Pyrrole-3-acetic acid, 1-[(4-methylphenyl)sulfonyl]-, methyl ester

138779-98-3
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86688-96-2
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Yield: 94%

Reaction Conditions:

Stage #1:N-tosyl-(1H-pyrrol-3-yl)acetic acid methyl ester with sodium hydroxide in methanol;water for 2 h;Reflux;
Stage #2: with hydrogenchloride in water; pH=3

Steps:

1.8 4.1.8
3-Acetic acid pyrrole (11)
2.87 mL NaOH (5 N) in 2.30 mL methanol was added to N-tosyl-3-methylacetatel pyrrole 10 (260.8 mg, 0.89 mmol) and refluxed for 2 h.
The methanol was removed and the residue was washed with diethyl ether and acidified by using a gradient of aqueous HCl in the range of 5 N-0.5 N to pH 3, and finally extracted four times with diethyl ether.
The solution was dried over Na₂SO₄ anhydrous.
After removal of the solvent, 3-acetic acid pyrrole 11 was obtained as a white solid (yield 105 mg, 0.84 mmol, 94%).
The product was recognized by ¹H NMR spectra
[16]
.

References:

Serra Moreno, Judith;Agas, Dimitrios;Sabbieti, Maria Giovanna;Di Magno, Matteo;Migliorini, Antonella;Loreto, M. Antonietta [European Journal of Medicinal Chemistry,2012,vol. 57,p. 391 - 397]