I am planning to use dess-martin periodinane and other hypervalent iodine reagents in reactions. Is there any special work up procedures to remove the byproducts of these reagents. Do the byproducts interfere in column chromatography?
In my experience, just one or two washes with 1M NaOH, one water wash. Drying/concentrate... ready for chromatography.
Reaction mixture was quenched with saturated sodium thiosulphate solution. The product was extracted with DCM or Chloroform. The organic layer was washed with saturated sodium bicarbonate solution and brine solution. After drying organic layer over anhydrous sodium sulphate, the solvent was evaporated under reduced pressure and purified by flash column chromatography
The reduced product of DMP after oxidation is IBA. It is insoluble in common organic solvents. Just do a simple filtration to remove it. If you use excess DMP, add few ml of water. It will hydrolyse DMP to insoluble IBX. Filter the precipitated IBA and IBX, using any common organic solvents, depending on the solubility of your product (DCM, chloroform, acetone, EtOAc, no alcohol). Then, perform column purification for the filtrate. The filtrate may have acetic acid residue, which can be removed under vacuums or bicarbonate treatment.
- reaction mass quench with saturated sodium bicarbonate solution and extracted with DCM,OR EtoAC, As per your compound solubility OR
- Reaction mass was quenched with sodium hypo chloride solution and combine organic layer was washed with sodium bicarbonate solution and dry by using na2so4 and concentrate we get crude compound
Work up of Dess-Martin periodinane involves simple filtration of the reduced product . By adding With few ml of water will hydrolyse DMP to insoluble IBX. Then filter precipitated IBA and IBX, using any common organic solvents, depending on the solubility of your product. Different solvents can be used such as DCM, chloroform, acetone, EtOAc instead of alcohols.
The conversion of primary and secondary alcohols into carbonyl compounds by the oxidation with a hypervalent iodine compound is known as the Dess–Martin periodinane oxidation. The oxidation of substrates containing sensitive functionalities is done by this reagent.
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