Selective monoalkylation of tetraethylene glycol

CHED 440

Ying Chau Liu, yliu8@mymail.indstate.edu, Kiersten Yake, and Richard W. Fitch, rfitch@indstate.edu. Department of Chemistry, Indiana State University, 600 Chestnut Street, Science S35E, Terre Haute, IN 47809
Monofunctionalized polyethylene glycols (PEGs) are useful synthons for a variety of polymeric materials. We have particular interest in these compounds for the synthesis of monodisperse linear and dendritic polymers for biological applications owing to the hydrophilicity and biological inertness of the PEG backbone. We have begun our investigations by investigating the monoalkylation of tetraethylene glycol as it is the largest readily available and inexpensive PEG oligomer. We have examined the monomethylation and monobenzylation of this diol and were able to exceed the anticipated yield from statistical distribution (50%) by varying the amount and type of base used for a standard Williamson ether synthesis. The design and results of our experiments will be discussed.