Something interesting about C5H9ClO

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Ethyl vinyl ether, MEM chloride, and dihydropyran based acetals of homoallylic and homopropargylic alcohols cyclize in the presence of Lewis acids to give 4-halotetrahydropyrans and 4-halo-5,6-dihydro-2H-pyrans, respectively.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics