Synthesis of alkylpyrroles by use of a vinamidinium salt

Tetrahedron Letters

Volumn 51, Issue 31, 2010, Pages 4150-4152

  Wright, Mathew T ^a   Carroll, David G ^a   Smith, Timothy M ^b   Smith, Stanton Q ^a  

^a VIRGINIA MILITARY INSTITUTE   (United States)

^b UNIVERSITY OF RICHMOND   (United States)

Author keywords

2 Pyrrolecarboxylate esters; Pyrroles; Vinamidinium salts

Indexed keywords

ALKYL GROUP; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; GLYCINE DERIVATIVE; PYRROLE DERIVATIVE; SODIUM CHLORIDE;

ARTICLE; POLYMERIZATION; SYNTHESIS;

EID: 77953959541     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.009     Document Type: Article

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16. General experimental procedure: All reagents and solvents were obtained from Aldrich, ACROS, or Fluka and used without further purification. To a flame dried one-necked round-bottomed flask equipped with magnetic stirring, reflux condenser, and nitrogen atmosphere (or drying tube) was added the vinamidinium salt (1.0 mmol) and glycine ester hydrochloride (2.0 mmol). Anhydrous acetonitrile (5 mL) was added via a syringe. Triethylamine (2.0 mmol) was added via a microliter syringe. The mixture was allowed to reflux overnight (15-18 h) under a nitrogen atmosphere (or drying tube). The flask was cooled to room temperature and the solvent was removed by rotary evaporation. The residue was partitioned between methylene chloride and water. The aqueous layer was extracted with fresh methylene chloride, and the combined organic layers were then dried over sodium sulfate. The drying agent was filtered and the solvents were removed in vacuo to give the crude material. The crude material was run through a short pad of silica gel with methylene chloride and the organic solvent was removed in vacuo. At this point the crude yield and percent purity were obtained. Analytical samples were obtained by either column chromatography with hexanes and ethyl acetate or low pressure distillation.
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