Indium mediated Barbier reactions of 1,2-diones: A facile synthesis of α-hydroxy ketones

Tetrahedron Letters

Volumn 41, Issue 7, 2000, Pages 1091-1094

  Nair, Vijay ^a   Jayan, C N ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

Barbier reactions; Diones; Indium

Indexed keywords

ALLYL ALCOHOL; ALLYL COMPOUND; BROMIDE; CINNAMYL ALCOHOL; DIKETONE; INDIUM; KETOL; SODIUM IODIDE;

ARTICLE; COLUMN CHROMATOGRAPHY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0034639630     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02237-6     Document Type: Article

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17. Typical experimental procedure: A mixture of the 1,2-dione (1 mmol), allyl bromide(1.55 mmol) indium powder (Aldrich chemicals) (1.05 mmol) and sodium iodide (1.55 mmol) in dimethylformamide (3 mL) was stirred at 25°C until completion of the reaction (TLC). The reaction mixture was quenched with a few drops of 1N HCl and extracted with diethylether. Evaporation of the solvent followed by purification of the product by silica gel column chromatography provided the pure product.
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19. 13C NMR 42.03, 79.79, 120.98, 122.25, 122.69, 125.36, 126.29, 127.42, 128.32, 128.48, 128.74, 130.67, 132.03, 134.99, 137.05, 139.44, 141.32, 205.17; CHN calcd: C(83.98), H(5.37). Observed: C(83.86), H(5.44).
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