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8.2.2.2.3 Variation 3: Etherification on Solid Support

DOI: 10.1055/sos-SD-008-00607

Venturello, P.; Barbero, M.Science of Synthesis, (20068897.

The Williamson ether synthesis on solid support has been developed.[‌11‌] The study involved substitution of a resin-bonded bromide (an ω-bromo alcohol) with primary alkoxides, derived from hexan-1-ol (9, R1=H) and 2-ethylhexan-1-ol (9, R1=Et) (Scheme 6).[‌11‌] The results indicate that on solid support the reaction to give ethers 10 suffers from severe competition from elimination of hydrogen bromide, to give alkenes 11, even when primary alkyl halides are used.

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