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Dess-Martin Oxidation of Allylic Alcohols; Enones

SyntheticPage 126
DOI: 10.1039/SP126
Submitted Aug 23, 2001, published Aug 23, 2001
zac etheridge (zac.etheridge@orange.net)
A contribution from Caddick, Sussex


			Reaction Scheme: <IMG src="/images/empty.gif">Dess-Martin Oxidation of Allylic Alcohols<IMG src="/images/empty.gif">

Chemicals Used

Dess Martin periodinane
Dicholoromethane (distilled from CaH2)
trans, trans-3-Acetoxy-5-hydroxy-4-tbutyldimethylsiloxy-cyclopentene

Procedure

The alcohol (40mg, 0.15mmol) is stirred at room temperature in DCM (3mL) under an inert atmosphere and the periodinane (99mg, 0.236mmol) is added in one portion. The reaction is stirred until completion (TLC, about 2 hours) then quenched with sodium thiosulphate (saturated solution), extracted 4 times with ethyl acetate, washed wiht brine, dried over magnesium sulphate, filtered and concentrated in vacuum. The product is purified by column chromatogrpahy using a short column (very little impurity) eluting with 30% EtOAc/PE to yield about 36mg (90%) of colourless oil.

Author's Comments

The Dess-Martin oxidation is very simple and versatile, and also tolerant of most functional groups. The oxidant can be made Page 51 or purchased from Lancaster.

Data

1H NMR (300MHz, CDCl3) 7.23 (1H, dd, J=1.7, 6.4), 6.17 (1H, d, J=6.0), 5.54 (1H, m), 4.15 (1H, d, J=2.6), 2.01 (3H, s), 0.79 (9H, s), 0.04 (3H, s), 0.00 (3H, s).

Lead Reference

S.Caddick et al Tetrahedron 2001 p6295

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Keywords: alcohol, oxidation, ketone, aldehyde, Dess-Martin, enone, allylic alcohol, 126

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