Swern oxidation
- Page ID
- 15019
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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
