A convenient one-pot, organoaluminum mediated vinylsilane synthesis from non-enolizable ketones via the Peterson protocol

Tetrahedron Letters

Volumn 43, Issue 48, 2002, Pages 8765-8768

  Kwan, Man Lung ^a,b   Battiste, Merle A ^a  

^a University of Florida ^*  (United States)

^b JOHN CARROLL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; HALIDE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VINYLSILANE; WATER;

ARTICLE; CHEMICAL BOND; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037175476     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02074-9     Document Type: Article

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31. 2Li (1 M) was added to a solution of ketone (500 mg) in xylene in a schlenk flask. After stirring at room temperature for 15 min, 1.4 equiv. of diethylaluminum chloride (1.8 M in toluene) and then 0.1 equiv. of water in THF (1 M) were added, forming a white cloudy solution. The tube was closed, then heated under reflux for 22-27 h (see Table 1 ). The resulting mixture was washed with a 20 mL mixture of 0.5 % sodium carbonate solution and extracted with ether. The combined ether extract was dried over anhydrous sodium sulfate for 15 min and evaporated. Reduced pressure distillation afforded a clear oil.
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