Procedure: 25 mL 1-neck flask, stirbar, septum, N2 inlet
Dissolved 0.077 mL of oxalylchloride (II) in 4.0 mL of dry CH2Cl2. Stirred; cooled to -78 C. Added 0.125 mL of DMSO. Stirred 10 min. Added a solution of 0.096 g of alcohol I in 1.0 mL of CH2Cl2. Stirred 15 min. Added 0.250 mL Et3N. After 15 min, warmed to 0 C. After 10 min TLC showed complete reaction. The reaction mixture was placed on a silica gel column and the product was isolated by flash chromatography .
notes
1. temp is critical for high yielding.
2. other than oxalylchloride, many activator can be used to overcome problem caused by oxalylchloride (ex. Cl-), ex. P2O5.
cited from
http://www.alsnotebook.com/oxidswern.html
Tuesday, May 5, 2009
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7 comments:
how did you add DMSO, alcohol and base to the reactor?
was it drop by drop?
what alcohol did you use?
yes, DMSO was added dropwise because the adding is violent.
the alcohol was an usually secondary alcohol.
Would this same protocol work for a primary alcohol?
yes it should do
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