Salicylic aldehydes were readily alkylated with (chloromethyl)trimethylsilane to give silylated ortho-methoxy benzaldehydes in 85–96 % yields. These aldehydes were converted into alkyl and aryl imines in excellent yields. O-(Trimethylsilyl)methyl moiety was applied as the synthetic equivalent of aryloxymethyl anion in the nucleophilic cyclization at the imine group promoted by CsF in DMF at 140 °C. Using this traceless methodology, 2,3-dihydrobenzofuran-3-amines were synthesized from salicylic aldehydes in 25–55 % yields in three steps.