Sodium Iodide → N,N-Diethyl-2-[(iodomethyl)dimethylsilyl]-1-naphthalenecarboxamide

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Reaction Steps

A solution of this naphthalenecarboxamide (1.0 g, 3.0 mmol) and NaI (13.5 g, 90 mmol) in acetonitrile (90 mL) was refluxed overnight, then was diluted with ether and filtered through celite to remove most of the salts. The filtrate was then concentrated and eluted through a plug of silica gel with ethyl acetate. Concentration of the ethyl acetate afforded 1.25 g of the desired compound as a yellow oil, a 98% yield.

Provenance & Evidence