Dess-Martin Oxidation of Allylic Alcohols; Enones
Submitted Aug 23, 2001, published Aug 23, 2001
Dess Martin periodinane
Dicholoromethane (distilled from CaH2)
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.
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).
S.Caddick et al Tetrahedron 2001 p6295
Keywords: alcohol, oxidation, ketone, aldehyde, Dess-Martin, enone, allylic alcohol, 126