A regioselective etherification of pyridoxine an -pyridinone methide intermediate.

The catalyst-free, regioselective synthesis of 4'-O-substituted pyridoxine derivatives under solventless conditions is described. The methodology relies on the highly regioselective formation of the -pyridinone methide from pyridoxine and subsequent oxa-Michael addition of alcohol nucleophiles. This methodology provides good to excellent yields for primary and secondary alcohols and moderate yields for tertiary alcohols.