36609-96-8Relevant academic research and scientific papers
Liquid-Liquid Extraction Protocol for the Removal of Aldehydes and Highly Reactive Ketones from Mixtures
Boucher, Maria M.,Furigay, Maxwell H.,Quach, Phong K.,Brindle, Cheyenne S.
, p. 1394 - 1403 (2017/09/23)
The reaction of the bisulfite ion with aldehydes to form charged bisulfite adducts is a well-established method for the purification of aldehydes. This reaction has been modified to create a convenient liquid-liquid extraction method for the removal of aldehydes from mixtures. The use of a water-miscible solvent allows the reaction to occur during a simple 30 s shaking protocol by increasing the contact between the bisulfite ion and the aldehyde. The introduction of an immiscible solvent allows for the extraction of the uncharged organic components away from the bisulfite adduct. The developed protocol is applicable to a wide range of aldehydes, including sterically hindered neopentyl aldehydes. Sterically unhindered cyclic and linear ketones, as well as highly electrophilic ketones, are also removed using this protocol. The mild conditions tolerate a wide range of functional groups, allowing for excellent aldehyde contaminant removal rates with high levels of recovery of the desired component.
Reduction of Weinreb amides to aldehydes under ambient conditions with magnesium borohydride reagents Dedicated to the memory of Professor Sheldon Shore
Bailey, Christopher L.,Clary, Jacob W.,Tansakul, Chittreeya,Klabunde, Lucas,Anderson, Christopher L.,Joh, Alexander Y.,Lill, Alexander T.,Peer, Natalie,Braslau, Rebecca,Singaram, Bakthan
supporting information, p. 706 - 709 (2015/01/30)
Chloromagnesium dimethylaminoborohydride (ClMg+ [H3BNMe2]-, MgAB) is an analogue of the versatile lithium dialkylaminoborohydrides (LAB reagents), prepared by the reaction of dimethylamine-borane with methylmagnesium chloride. MgAB is a partial reducing agent for Weinreb amides under ambient conditions and is complementary to the commonly utilized lithium aluminum hydride (LiAlH4) and diisobutylaluminum hydride (DIBAL) reagents, while exhibiting enhanced chemoselectivity. To prevent over-reduction, the aldehyde products are readily isolated in good yields by forming the sodium bisulfite adducts. Aldehyde products can both be stored and later used as the bisulfite adducts, or can be regenerated from the bisulfite adducts by treatment with aqueous formaldehyde.
