Synthesis
The Preparative Method of tributyl((methoxymethoxy)methyl)stannane: The most convenient preparation involves the two-step procedure outlined in eq 1. The first step involves the addition of Tri-n-butylstannyllithium to Paraformaldehyde, as Still described. In the second step, methoxymethylation is achieved via acetal exchange with Dimethoxymethane, promoted by Boron Trifluoride Etherate and Molecular Sieves. This procedure provides the desired reagent in higher yields compared to an alternative procedure which uses Phosphorus(V) Oxide to promote the acetal exchange step. This method is also superior to an alternative approach, which involves alkylation of (tributylstannyl)methanol with Chloromethyl Methyl Ether.
Precautions
As with all organostannanes, precautions should be taken to avoid all contact with tributyl[(methoxymethoxy)methyl]stannane. The reagent should be handled in a fume hood. The reagent can be stored neat in a freezer under nitrogen for several months.
