N,4,4-Trimethyl-2-oxazolinium Iodide

[30093-97-1]  · C6H12INO  · N,4,4-Trimethyl-2-oxazolinium Iodide  · (MW 241.09)

(a formylation and deuteroformylation reagent for aryl, benzyl, vinyl, and alkynyl Grignard reagents1,2)

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.

Synthetic Utility.

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

Related Reagents.

Diethyl Phenyl Orthoformate; N,N-Dimethylformamide; N,N-Dimethylformamide Diethyl Acetal; N,O-Dimethylhydroxylamine; 1,1,3,3-Tetramethylbutyl Isocyanide; Triethyl Orthoformate.

1. Meyers, A. I.; Collington, E. W. JACS 1970, 92, 6676.
2. Brinkmeyer, R. S.; Collington, E. W.; Meyers, A. I. OSC 1988, 6, 64.

Todd D. Nelson & Albert I. Meyers

Colorado State University, Fort Collins, CO, USA

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