[30093-97-1] · C6H12INO · N,4,4-Trimethyl-2-oxazolinium Iodide · (MW 241.09)
Physical Data: mp 215 °C (dec).
Preparative Method: by alkylation of commercially available 4,4-dimethyl-2-oxazoline with Iodomethane (eq 1). Filtration and purification affords the 2-oxazolinium salt in 80% yield.1
Handling, Storage, and Precautions: slightly hygroscopic; store under an inert atmosphere; use in a fume hood.
N,4,4-Trimethyl-2-oxazolinium iodide is used as a formylating reagent. Aryl, vinyl, benzyl, and alkynyl Grignard reagents react with the title compound in the presence of HMPA to form the corresponding oxazolidine adducts (eq 2, Table 1).1 Hydrolysis of the oxazolidine with Oxalic Acid releases the free aldehyde. However, aliphatic Grignard reagents do not successfully enter into this protocol.1,2
Utilization of deuterated N,4,4-trimethyl-2-oxazolinium iodide affords the corresponding deuterated aldehyde (eq 3).1
Diethyl Phenyl Orthoformate;
Todd D. Nelson & Albert I. Meyers
Colorado State University, Fort Collins, CO, USA