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Volumn 10, Issue 10, 2008, Pages 1927-1930

New, general, and practical preparation of methyl ketones via the direct coupling of amides with CH2CI2 promoted by TiCI 4/Mg

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; DICHLOROMETHANE; KETONE; MAGNESIUM; TITANIUM; TITANIUM TETRACHLORIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMIDES; KETONES; MAGNESIUM; METHYLENE CHLORIDE; MOLECULAR STRUCTURE; STEREOISOMERISM; TITANIUM;

EID: 47049085836 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol8004326 Document Type: Article

Times cited : (20)

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- The following procedure for the synthesis of 4-phenyl-2-butanone 2a is illustrative. To a 0 °C suspension consisting of Mg (192 mg, 8 mmol) and TiCl4 (1.5 mmol, 1 M in CH2Cl2, 1.5 mL) in CH2C12 (4 mL) was added over a 2 min period a solution of amide 1a (219 mg, 1 mmol) in CH2C12 (5 mL) and THF (2 mL, After being stirred for 1 min at 0 °C, the resulting greenback mixture was stirred for an additional 1 h at 0 °C. Saturated potassium carbonate solution (10 mL) was added, and the mixture was diluted with CH2C12 (25 mL, The organic layer was separated, dried, evaporated, and purified by flash chromatography on silica gel (elution with 1:15 ethyl acetate-hexane) to give 2a (126 mg, 85% yield) as a colorless oil. See the Supporting Information for characterization. In the case of aromatic amide 3, treatment under the above conditions gives the desired
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