N-Methyl-N-trimethylsilylmethyl-N'-tert-butylformamidine

Chemical Properties

CLEAR PALE YELLOW LIQUID

Uses

N-METHYL-N-TRIMETHYLSILYLMETHYL-N'-TERT-BUTYLFORMAMIDINE conveniently effects the transformation of ketones and aldehydes to homologated nitriles, amines, aldehydes, and ketones.

Synthesis

N-METHYL-N-TRIMETHYLSILYLMETHYL-N'-TERT-BUTYLFORMAMIDINE is easily synthesized by a two-step procedure (eq 1).1 Initially, the condensation of t-Butylamine with either N,N-Dimethylformamide or dimethylformamide dimethyl acetal cleanly affords N′-t-Butyl-N,N-dimethylformamidine. Subsequent lithiation and silylation with Chlorotrimethylsilane results in a 70% overall yield of the purified title reagent.

storage

The reagent should be handled in a fume hood. Refrigeration should be used for prolonged storage.