The Smythe reagent is an approximately 1.6 M suspension of LiOH in hexane, and is ubiquitous in synthetic chemistry laboratories worldwide. While commercially available, it is more frequently prepared from n-butyllithium, usually by accident. We describe a range of applications for this reagent, such as the O-lithiation of carboxylic acids, hydrolysis of ethyl esters and chlorophosphines, racemisation of alpha-stereocenters and poly-Claisen condensations.

Burnie Urethra’s group have set themselves a Herculean task: the total synthesis of Impracticatechol (1). The highly complicated structure features a dozen stereocenters and a raft of functional groups including a pentavalent carbon. This malevolent moiety constitutes a significant challenge to the synthetic chemist, as until now, no methodology has been reported pertaining to their preparation. Herein, we describe an easy and promiscuous protocol for generating pentavalent carbon centers via a one-pot curse-transfer cyclisation reaction, inspired by r/cursed_chemistry.