the boekelheide reaction is a rearrangement of α-picoline-"n"-oxides to hydroxymethylpyridines. it is named after virgil boekelheide who first reported it in 1954. originally the reaction was carried out using acetic anhydride, which typically required a period at reflux (~140°c). the reaction can be performed using trifluoroacetic anhydride (tfaa), which often allows for a room temperature reaction.