Practical Reactions / Oxidation

Dess-Martin Oxidation

Preparation of (3as, 6S, 6aS)-(9H-fluoren-9-yl)methyl 6-tert-butoxy-3- oxotetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate (4c).
Alcohol (4b) (70 mg, 0.165 mmol) was dissolved in anhydrous dichloromethane (5 mL) with stirring under argon. Dess-Martin periodinane (141 mg, 0.33 mmol) was added and the mixture stirred for 2 h. The mixture was diluted with DCM (20 mL) and washed with sat. NaHCO3 / 0.25M Na2S2O3, sat. NaHCO3, brine (25 mL each) and dried (Na2SO4). The organic layer was filtered and reduced in vacuo to leave a clear film (∼ 110 mg). The crude film was purified on a 5g Flash silica cartridge eluting with a gradient of heptane : ethyl acetate 7:1→ 2:1 to provide ketone (4c) as a colourless gum (70.5 mg, 0.165 mmol, 99.8%).

WO2008007132

Dess-Martin Periodinane / 87413-09-0

デス・マーチン酸化 Dess-Martin Oxidation
Dess-Martin Oxidation - Organic Chemistry Portal

・後処理は、NaHCO3/Na2S2O3 水溶液を加えて、クエンチすることが多い。もしくは、反応溶媒を除去して、そのままカラム精製する。

・１等量の水を添加すると、反応が加速されることが知られている。（10.1021/jo00103a067)