Benzylation of β-dicarbonyl compounds and 4-hydroxycoumarin using TMSOTf catalyst: A simple, mild, and efficient method

Tetrahedron Letters

Volumn 51, Issue 41, 2010, Pages 5454-5458

  Theerthagiri, Palani ^a   Lalitha, Appaswami ^a  

^a PERIYAR UNIVERSITY   (India)

Author keywords

Dicarbonyl compounds; 4 Hydroxycoumarin; Benzylation; Benzylic alcohols; TMSOTf catalyzed

Indexed keywords

1,3 DICARBONYL DERIVATIVE; 4 HYDROXYCOUMARIN; BENZYL ALCOHOL; KETONE; SULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID TRIMETHYLSILYL ESTER; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BENZYLATION; CATALYST; CHEMICAL STRUCTURE; ROOM TEMPERATURE;

EID: 79953189453     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.019     Document Type: Article

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36. General experimental procedure for the TMSOTf-catalyzed alkylation of 1,3-dicarbonyl compounds: To a mixture of alcohol (1 mmol) and 1,3-dicarbonylcompound (2 mmol) in nitro methane (10 vol), TMSOTf (15 mol %) was added drop wise. The reaction mixture was stirred at room temperature for 30 min. After completion of the reaction (monitored by TLC), water was added and extracted with EtOAc, the organic layer was separated and washed with water, brine and dried over sodium sulfate and concentrated to furnish the desired compound. When necessary, the obtained crude sample was purified by column chromatography.
37. 2 (10 ml), TMSOTf (0.15 mmol) was added and the reaction mixture was stirred for the given time (see Table 2) at room temperature. After completion of the reaction (monitored by TLC), to the reaction mixture was added water and extracted with ethyl acetate, the combined organic phase was dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by silica gel column with hexane/ethyl acetate as eluent to afford the corresponding C3-alkylated 4-hydroxycoumarin.