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An efficient, two-step synthetic method for the addition of ethyleneoxy units to diols is reported.Reaction of HOROH with Cl(CH2CH2O)nTHP and 50percent aqueous NaOH in the presence of a phase-transfer catalyst gives THP(OCH2CH2)nORO(CH2CH2O)nTHP from which the protecting groups are readily removed to provide H(OCH2CH2)nORO(CH2CH2O)n in good-to-excellent yields.The influence of reactant diol structure upon yield has been determined.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics