A new method for the lactonization of ω-hydroxy carboxylic acids with Di-2-thienyl carbonate by the promotion of DMAP and iodine

Chemistry Letters

Volumn 34, Issue 1, 2005, Pages 72-73

  Oohashi, Yoshiaki ^a   Fukumoto, Kentarou ^a   Mukaiyama, Teruaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; IODINE; LACTONE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; LACTONIZATION; SYNTHESIS;

EID: 17144414184     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.72     Document Type: Article

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20. 3CN (10 mL) was added DMAP (1.08 mg, 0.0088 mmol). After stirring for 15 min at room temperature, the resultant solution was diluted by the addition of 166 mL of toluene and treated with iodine (179 mg, 0.707 mmol). The reaction mixture was stirred for 10 h at reflux temperature of toluene and then 10% aqueous sodium thiosulfate was added and the solvent was evaporated. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and brine, dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by preparative thin layer chromatography to afford the corresponding lactone (26.8 mg, 77%).