The pyrrole approach toward the synthesis of fully functionalized cup-shaped molecules

Organic Letters

Volumn 7, Issue 6, 2005, Pages 1003-1006

  Zonta, Cristiano ^a   Fabris, Fabrizio ^a   De Lucchi, Ottorino ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; MOLECULAR INTERACTION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 18244408784     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047569f     Document Type: Article

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19. General Procedure for the Synthesis of 3. A solution of bromine (7.4 mL, 0.14 mol) in acetic acid (80 mL) was slowly added to a solution of 2 (13.5 g, 0.06 mol) in acetic acid (200 mL) over 30 min. After addition was completed the mixture was heated to reflux for 1.5 h. The reaction mixture was warmed to room temperature and the solvent removed under reduced pressure. The black oil was filtered through a column of silica using DCM as eluant. The resulting oil was recrystallised in a DCM/ether mixture giving 3 (6.5 g) as colorless crystals. The remaining oil was then purified using silica flash chromatography (DCM) affording further 3.5 g of product with an overall yield of 43%.
20. +].
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