Microwave-assisted Ketone-Ketone rearrangement: An improved synthesis of 3-(4-alkoxyphenyl)-3-methylbutan-2-ones

Organic Letters

Volumn 4, Issue 5, 2002, Pages 781-782

  Gopalakrishnan, Geetha ^a   Kasinath, Viswanathan ^a   Singh, N D Pradeep ^a  

^a Spic Science Foundation India   (India)

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Indexed keywords

EID: 0037916247     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017265i     Document Type: Article

References (14)

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8. Shuttleworth, S.J.; Allin, S.M.; Wilson, R.D.; Naustirica, D. Synthesis 2000, 1035.
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11. 4). Removal of the solvent followed by column chromatography (ethyl acetate/hexane 5:95) of the crude product yielded 3-(4-hydroxy-phenyl)-3-methylbutan-2-one (II) (0.288 g. 75%).
12. 13C NMR 213.2, 155.0, 135.6, 127.2, 115.7, 51.9, 25.5, 25.2.
13. -) was packed in a column, and compound II (5 g) in o-dichlorobenzene was repeatedly passed through the column until compound II was completely adsorbed as phenoxide ion. The phenoxide resin thus prepared (2 g resin/ 200 mg of II, 1.14 mmol) was reacted with various alkylating agents (1.5 mmol) in THF in a modified domestic microwave oven with refluxing unit. After the completion of reaction (TLC), the reaction mixture was filtered and the solvent was removed. The residue on column chromatography yielded the respective 3-(4-alkoxyphenyl)-3methylbutan-2-ones IIIa-j (Table 2).
14. + mlz) 290.