Swern oxidation

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Below is a standard procedure for the Swern oxidation of an alcohol.

Procedure

To a solution of oxalyl chloride (5 mmol) and 3 Å MS in CH₂Cl₂ (1 mL) at -78 °C under N₂ is added dropwise a solution of DMSO (10 mmol) in CH₂Cl₂ (1 mL). After 15 min a solution of the alcohol in CH₂Cl₂ (3 mL) is slowly added dropwise. After 30 min, Et₃N (15 mmol) is added dropwise. The reaction is stirred 30 min at -78 °C then slowly allowed to warm to rt.

Notes:

Dichloromethane is usually the solvent of choice for this reaction, but Et₂O or THF may also be used.
For secondary alcohols, warming the reaction to -40 °C after the addition of the alcohol for 20 min may help.
Bulkier amines such as diisopropylethylamine can be used instead of triethylamine in case of epimerization of the α-center

Mechanism

Contributors

OChemOnline

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