N-Benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine

[93102-05-7] C13H23NOSi (MW 237.42) InChI = 1S/C13H23NOSi/c1-15-11-14(12-16(2,3)4)10-13-8-6-5-7-9-13/h5-9H,10-12H2,1-4H3 InChIKey = RPZAAFUKDPKTKP-UHFFFAOYSA-N (nonstabilized azomethine ylide precursor;1 reacts with alkenes to give pyrrolidines;2 alkynes give 3-pyrrolines;2 carbonyl and thiocarbonyl groups afford 1,3-oxazolidines and 1,3-thiazolidines, respectively3) Physical Data: bp 77–80 °C/0.5 mmHg. Preparative Methods: most conveniently prepared by treatment of benzylamine with chloromethyltrimethylsilane followed by formaldehyde and methanol.4 Access to higher ether homologs is achieved by replacing methanol with the appropriate alcohol.5 An alternate procedure involves alkylation of lithium N-benzyltrimethylsilymethylamide with methoxymethyl chloride.2 Purification: distillation under reduced pressure, although good yields can be obtained with undistilled reagent. Handling, Storage, and Precautions: the reagent should be handled in a well ventilated fume hood.