Friday, October 15, 2010

deprotection of dimethyl acetal

1. in a particular substrate bearing a terminal double bond at 5,6 position related to the acetal,
the following deprotection methods failed

Methods tried:                                 results:

1. TFA/water/chloroform                   unknown product, aldehyde/alkene disappeared

2. I2/acetone                                     unknown product, aldehyde/alkene disappeared

3.HCOOH, pentane                          unknown product, aldehyde/alkene disappeared

4. TESOTf, 2,6-lutidine                       no reaction

the following method is successful:

DDQ/MeCN/water rt.