An efficient method for removal of ruthenium byproducts from olefin metathesis reactions

Organic Letters

Volumn 5, Issue 4, 2003, Pages 531-533

  Cho, Jong Hyun ^a   Kim, B Moon ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED CARBON; ALKENE; CHEMICAL COMPOUND; PETROLEUM; RUTHENIUM; SILICON DIOXIDE;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; RING CLOSING METATHESIS;

EID: 0141518449     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027423l     Document Type: Article

References (32)

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31. Reference 8 describes in detail the sampling procedure for determination of the levels of residual ruthenium in the RCM products.
32. Procedure for RCM of 4 and purification of crude product 5 with silica gel and activated carbon (method B): To a stirred solution of 300 mg of diethyl diallylmalonate (4, 1.25 mmol) in degassed dichloromethane (500 mL) was added catalyst 1 (100 mg, 10 mol %) under argon atmosphere at room temperature. After the reaction mixture was stirred for 2 h, the dark solution was adsorbed on silica gel (1.0 g, 10 equiv wt, relative to catalyst 1) and passed through a pad of silica gel (hexane:EtOAc ratio 6:1 to 2:1). The filtered solution was stirred with activated charcoal (12.0 g, 50 equiv wt of 5) for 12 h. After the carbon was filtered, the filtrate was concentrated in vacuo and purified on a silica gel chromatographic column (hexane:EtOAc ratio 5:1) to provide product 6 as a colorless oil in 90% yield.